Light-emitting device using organometallic complex

ABSTRACT

Light-emitting elements having high emission efficiency and long lifetime can be provided. By forming light-emitting devices including the light-emitting elements, the light-emitting devices having low power consumption and long lifetime can be provided. A light-emitting device comprises a light-emitting element including a light-emitting layer between a first electrode and a second electrode. The light-emitting layer includes a first organic compound having a hole-transporting property, a second organic compound having an electron transporting property, and an organometallic complex. A central metal of the organometallic complex is an element belonging to one of Group 9 and Group 10, and a ligand of the organometallic complex is a ligand having a pyrazine skeleton.

TECHNICAL FIELD

The present invention relates to light-emitting elements using aphosphorescent compound. Further, the present invention relates tolight-emitting devices using the light-emitting element. Moreover, thepresent invention relates to electronic devices using the light-emittingdevice.

BACKGROUND ART

In recent years, a light-emitting element using a light-emitting organiccompound or inorganic compound as a light-emitting substance has beenactively developed. In particular, a light-emitting element called an ELelement has a simple structure in which a light-emitting layercontaining a light-emitting substance is provided between electrodes.Therefore, the light-emitting element has attracted attention as anext-generation flat panel display element because of itscharacteristics such as a thin shape, lightweight, high response speed,and direct current driving at low voltage. In addition, a display usingsuch a light-emitting element has a feature that it is excellent incontrast and image quality, and has a wide viewing angle. Further, sincethese light-emitting elements are plane light sources, it is consideredthat these light-emitting elements are applied as light sources such asa backlight of a liquid crystal display and an illumination device.

In a case of using a light-emitting organic compound as a light-emittingsubstance, the emission mechanism of a light-emitting element is acarrier injection type. Namely, by application of a voltage with alight-emitting layer interposed between electrodes, carriers (holes andelectrons) injected from the electrodes are recombined and thus alight-emitting substance is made to be in an exited state. Light isemitted when the excited state returns to the ground state. As the typeof the excited state, a singlet excited state (S*) and a triplet excitedstate (T*) are possible. The statistical generation ratio thereof in alight-emitting element is considered to be S*:T*=1:3.

In general, the ground state of a light-emitting organic compound is asinglet excited state. Therefore, light emission from a singlet excitedstate (S*) is referred to as fluorescence because it is caused byelectron transition between the same multiplicities. On the other hand,light emission from a triplet excited state (T*) is referred to asphosphorescence because it is caused by electron transition betweendifferent multiplicities. Here, in a compound emitting fluorescence(hereinafter referred to as a fluorescent compound), in general,phosphorescence is not observed at room temperature, and onlyfluorescence is observed. Therefore, in a light-emitting element using afluorescent compound, the theoretical limit of internal quantumefficiency (the ratio of generated photons to injected carriers) isconsidered to be 25% based on S*:T*=1:3.

On the other hand, when a compound emitting phosphorescence (hereinafterreferred to as a phosphorescent compound) is used, internal quantumefficiency can be theoretically 75 to 100%. In other words, luminousefficiency can be three to four times as high as that of a fluorescentcompound. From these reasons, in order to achieve a light-emittingelement with high efficiency, a light-emitting element using aphosphorescent compound has been proposed (for example, Non PatentDocument 1 TSUTSUI et al., HIGH QUANTUM EFFICIENCY IN ORGANICLIGHT-EMITTING DEVICES WITH IRIDIUM-COMPLEX AS A TRIPLET EMISSIVECENTER, JPN. J. APPL. PHYS. (JAPANESE JOURNAL OF APPLIED PHYSICS), vol.38/PART. 2, No. 12B, 15 Dec. 1999, pages L1502-L1504 and Non PatentDocument 2: ADACHI et al., HIGH-EFFICIENCY RED ELECTROPHOSPHORESCENCEDEVICES, APPL. PHYS. LETT. (APPLIED PHYSICS LETTERS), vol. 78, No. 11,12 Mar. 2001, pages 1622-1624. Non Patent Documents 1 and 2 employ aniridium complex using a ligand of 2-phenylpyridine (Ir(ppy)₃) and aligand of 2-(2′-benzo[4,5-a]thienyl)pyridine ([btp₂Ir(acac)]) asphosphorescent compounds, respectively.

Further, Patent Document 1 discloses a light-emitting element using alight-emitting layer which contains, as a host material for aphosphorescent dopant, an organic low molecular hole-transportingsubstance and an organic low molecular electron-transporting substancein order to improve the lifetime and efficiency of the light-emittingelement using a phosphorescent compound (Patent Document 1 JapaneseTranslation of PCT International Application No. 2004-515895).

DISCLOSURE OF INVENTION

Non Patent Document 1 reports a problem of lifetime, that is, ahalf-life period of luminance is about 170 hours at constant currentdriving at the initial luminance of 500 cd/m². In addition, Non PatentDocument 1 reports a problem of lifetime, in which BCP is used as ahole-blocking layer, because the stability of BCP is not sufficient.

However, if BCP is removed from the element structure disclosed in NonPatent Document 1, light cannot be emitted efficiently. This is becauseCBP used in the host material of the light-emitting layer in Non PatentDocument 1 has a strong hole-transporting property, holes may reach anelectron-transporting layer, if BCP is not used as the hole-blockinglayer. In addition, BCP has a function of blocking excitation energy (inthis case, triplet excitation energy) generated in the light-emittinglayer. Thus, the element structure of Non Patent Document 1 can achievehigh efficiency but cannot obtain long lifetime, due to BCP.

On the other hand, Patent Document 1 reports improvement in lifetime ofan element and efficiency. However, the performance of a phosphorescentcompound cannot be utilized efficiently. Actually, the light-emittingelement 1 of Patent Document 1 employs an iridium complex,[btp₂Ir(acac)], which is also used in Non Patent Document 2, and theefficiency is about 0.9 cd/A to 2.0 cd/A, which is still lower than theefficiency described in Non Patent Document 2.

For the above reasons, it is difficult to obtain a high efficiency andlong lifetime of a phosphorescent compound at the same time.Practically, light-emitting elements using phosphorescent compoundssecure lifetime at efficiency's expense somewhat.

In view of the above, it is an object of the present invention toprovide light-emitting elements having high efficiency and longlifetime. It is another object of the present invention to providelight-emitting devices with long lifetime which consumes less power byforming the light-emitting devices using the light-emitting elements.Further, it is still another object of the present invention to provideelectronic devices with long lifetime, which consumes less power byapplying such light-emitting devices to the electronic devices.

The present inventors have studied diligently and thus found that theabove problem can be solved by devising a structure of a light-emittinglayer including a light-emitting substance, in a light-emitting elementusing, as a light-emitting substance, a certain kind of organometalliccomplex having a strong electron-trapping property. Specifically, in alight-emitting element using, as a light-emitting substance, anorganometallic complex having a ligand of a pyrazine derivative, acompound having a hole-transporting property and a compound having anelectron-transporting property can both be included in thelight-emitting layer. This solution is found by the present inventors.

An aspect of the present invention is a light-emitting elementcomprising a light-emitting layer between a first electrode and a secondelectrode, the light-emitting layer including a first organic compoundhaving a hole-transporting property, a second organic compound having anelectron transporting property, and an organometallic complex. In thelight-emitting element, a ligand of the organometallic complex is aligand having a pyrazine skeleton, and a central metal of theorganometallic complex is an element belonging to Group 9 or an elementbelonging to Group 10.

Another aspect of the present invention is a light-emitting elementcomprising a light-emitting layer between a first electrode and a secondelectrode, the light-emitting layer including a first organic compoundhaving a hole-transporting property, a second organic compound having anelectron transporting property, and an organometallic complex. In thelight-emitting element, a ligand of the organometallic complex is a2-arylpyrazine derivative, and a central metal of the organometalliccomplex is an element belonging to Group 9 or an element belonging toGroup 10.

As the above 2-arylpyrazine derivative, a 2-phenylpyrazine derivative ispreferable. Thus, another aspect of the present invention is alight-emitting element comprising a light-emitting layer between a firstelectrode and a second electrode, in which the light-emitting layerincludes a first organic compound having a hole-transporting property, asecond organic compound having an electron transporting property, and anorganometallic complex. In the light-emitting element, a ligand of theorganometallic complex is a 2-phenylpyrazine derivative, and a centralmetal of the organometallic complex is an element belonging to Group 9or an element belonging to Group 10.

As the above 2-arylpyrazine derivative, in particular, a2,5-diphenylpyrazine derivative is preferable. Thus, another aspect ofthe present invention is a light-emitting element comprising alight-emitting layer between a first electrode and a second electrode,in which the light-emitting layer includes a first organic compoundhaving a hole-transporting property, a second organic compound having anelectron transporting property, and an organometallic complex. In thelight-emitting element, a ligand of the organometallic complex is a2,5-diphenylpyrazine derivative, and a central metal of theorganometallic complex is an element belonging to Group 9 or an elementbelonging to Group 10.

Note that in the above structures, the central metal is iridium orplatinum in terms of emission efficiency. In particular, iridium ispreferable since iridium can provide extremely high efficiency.

Specifically, the organometallic complex using a ligand having apyrazine skeleton is an organometallic complex having a structurerepresented by the following general formula (G1). Thus, another aspectof the present invention is a light-emitting element comprising alight-emitting layer between a first electrode and a second electrode,in which the light-emitting layer includes a first organic compoundhaving a hole-transporting property, a second organic compound having anelectron transporting property, and an organometallic complex, and theorganometallic complex has a structure represented by a general formula(G1).

In the formula, A_(r) represents an arylene group. R¹ represents eitheran alkyl group or an aryl group. R² represents hydrogen, an alkyl groupor an aryl group. R³ represents either hydrogen or an alkyl group. R²and R³ may be bound to each other to form an alicycle. M is a centralmetal, and represents either an element belonging to Group 9 or anelement belonging to Group 10.

As the organometallic complex having a structure represented by thegeneral formula (G1), an organometallic complex represented by thegeneral formula (G2) is preferable. Thus, another aspect of the presentinvention is a light-emitting element comprising a light-emitting layerbetween a first electrode and a second electrode, in which thelight-emitting layer includes a first organic compound having ahole-transporting property, a second organic compound having an electrontransporting property, and an organometallic complex, and theorganometallic complex has a structure represented by a general formula(G2).

In the formula, R¹ represents either an alkyl group or a phenyl group.R² represents hydrogen, an alkyl group or a phenyl group. R³ representseither hydrogen or an alkyl group. R² and R³ may be bound to each otherto form an alicycle. R⁴ to R⁷ represent any of hydrogen, an alkyl group,a halogen group, a haloalkyl group, an alkoxy group, and analkoxycarbonyl group. M is a central metal, and represents either anelement belonging to Group 9 or an element belonging to Group 10.

As the organometallic complex having a structure represented by thegeneral formula (G1), an organometallic complex represented by thegeneral formula (G3) is preferable in particular. Thus, another aspectof the present invention is a light-emitting element comprising alight-emitting layer between a first electrode and a second electrode,in which the light-emitting layer includes a first organic compoundhaving a hole-transporting property, a second organic compound having anelectron transporting property, and an organometallic complex, and theorganometallic complex has a structure represented by a general formula(G3).

In the formula, R¹ represents either an alkyl group or a phenyl group.R³ represents either hydrogen or an alkyl group. R⁴ to R¹² represent anyof hydrogen, an alkyl group, a halogen group, a haloalkyl group, analkoxy group, and an alkoxycarbonyl group. M is a central metal, andrepresents either an element belonging to Group 9 or an elementbelonging to Group 10.

More specifically, the organometallic complex having a structurerepresented by the general formula (G1) is an organometallic complexrepresented by the general formula (G4). Thus, another aspect of thepresent invention is a light-emitting element comprising alight-emitting layer between a first electrode and a second electrode,in which the light-emitting layer includes a first organic compoundhaving a hole-transporting property, a second organic compound having anelectron transporting property, and an organometallic complex, and theorganometallic complex has a structure represented by a general formula(G4).

In the formula, A_(r) represents an arylene group. R¹ represents eitheran alkyl group or an aryl group. R² represents hydrogen, an alkyl groupor an aryl group. R³ represents either hydrogen or an alkyl group. R²and R³ may be bound to each other to form an alicycle. In addition, M isa central metal, and represents either an element belonging to Group 9or an element belonging to Group 10. In addition, L is a monoanionicligand. When the M is an element belonging to Group 9, n is 2 (n=2) andwhen the M is an element belonging to Group 10, n is 1 (n=1).

More specifically, the organometallic complex having a structurerepresented by the general formula (G2) is an organometallic complexrepresented by the general formula (G5). Thus, another aspect of thepresent invention is a light-emitting element comprising alight-emitting layer between a first electrode and a second electrode,in which the light-emitting layer includes a first organic compoundhaving a hole-transporting property, a second organic compound having anelectron transporting property, and an organometallic complex, and theorganometallic complex has a structure represented by a general formula(G5).

In the formula, R¹ represents either an alkyl group or a phenyl group.R² represents hydrogen, an alkyl group or a phenyl group. R³ representseither hydrogen or an alkyl group. R² and R³ may be bound to each otherto form an alicycle. R⁴ to R⁷ represent any of hydrogen, an alkyl group,a halogen group, a haloalkyl group, an alkoxy group, and analkoxycarbonyl group. In addition, M is a central metal, and representseither an element belonging to Group 9 or an element belonging to Group10. L is a monoanionic ligand. In addition, when the M is an elementbelonging to Group 9, n is 2 (n=2) and when the M is an elementbelonging to Group 10, n is 1 (n=1).

More specifically, the organometallic complex having a structurerepresented by the general formula (G3) is an organometallic complexrepresented by the general formula (G6). Thus, another aspect of thepresent invention is a light-emitting element comprising alight-emitting layer between a first electrode and a second electrode,in which the light-emitting layer includes a first organic compoundhaving a hole-transporting property, a second organic compound having anelectron transporting property, and an organometallic complex, and theorganometallic complex has a structure represented by a general formula(G6).

In the formula, R¹ represents either an alkyl group or a phenyl group.R³ represents either hydrogen or an alkyl group. R⁴ to R¹² represent anyof hydrogen, an alkyl group, a halogen group, a haloalkyl group, analkoxy group, and an alkoxycarbonyl group. In addition, M is a centralmetal, and represents either an element belonging to Group 9 or anelement belonging to Group 10. L is a monoanionic ligand. When the M isan element belonging to Group 9, n is 2 (n=2) and when the M is anelement belonging to Group 10, n is 1 (n=1).

In addition, in the above general formulae (G1) to (G6), the M ispreferably iridium or platinum in terms of emission efficiency. Inparticular, iridium is preferable since iridium can provide extremelyhigh efficiency.

In the above light-emitting elements, the first organic compound ispreferably an aromatic amine compound or a carbazole derivative. Thesecond organic compound is preferably a heteroaromatic compound or ametal complex. More preferably, the first organic compound is anaromatic amine compound or a carbazole derivative and the second organiccompound is a heteroaromatic compound or a metal complex.

In the above light-emitting elements, an amount of the first organiccompound and/or an amount of the second organic compound is/arepreferably larger than that of the organometallic complex. In otherwords, the first organic compound and/or the second organic compoundpreferably function as a host of the organometallic complex. Morepreferably, an amount of the organometallic complex in thelight-emitting layer is greater than or equal to 1 percent by mass andless than or equal to 10 percent by mass.

In the above light-emitting elements, the ratio between the firstorganic compound and the second organic compound is also important.Therefore, in the light-emitting elements of the present invention, amass ratio of the second organic compound to the first organic compoundis preferably greater than or equal to 1/20 to less than or equal to 20.In particular, a mass ratio of the second organic compound to the firstorganic compound is preferably greater than or equal to 1 to less thanor equal to 20.

The above structures of the present invention are made in view of astrong electron-trapping property of the organometallic complexes. Thus,in the above light-emitting elements of the present invention, a LUMOlevel of the organometallic complex is deeper than a LUMO level of thefirst organic compound and a LUMO level of the second organic compoundby 0.2 eV or more.

A light-emitting element obtained in this manner of the presentinvention has a feature that emission efficiency is high and lifetime islong, and thus a light-emitting device (such as an image display deviceor a light-emitting device) using the light-emitting element can achievelow power consumption and long lifetime. Therefore, the presentinvention includes light-emitting devices using light-emitting elementsof the present invention. Furthermore, the present invention includeselectronic devices having the light-emitting devices.

It is to be noted that the light-emitting device in this specificationincludes image display devices and illumination devices using alight-emitting element. Further, the light-emitting device includesvarious types of modules e.g., a module in which a connector such as anFPC (Flexible Printed Circuit), a TAB (Tape Automated Bonding) tape, ora TCP (Tape Carrier Package) is attached to a light-emitting element, amodule in which a print wiring board is provided at an end of a TAB tapeor an TCP, and a module in which an IC (Integrated Circuit) is directlymounted on a light-emitting device by a COG (Chip On Glass) method.

According to the present invention, light-emitting elements having highemission efficiency can be provided. In particular, light-emittingelements having high emission efficiency and long lifetime can beprovided.

When light-emitting devices are formed using the light-emitting elementsdescribed above, the light-emitting devices can consume less power andhave long lifetime. Further, since such light-emitting devices areapplied to electronic devices, the electronic devices can have longlifetime, which consumes less power.

BRIEF DESCRIPTION OF DRAWINGS

In the accompanying drawings:

FIG. 1 is a band diagram of a light-emitting element according to anaspect of the present invention;

FIGS. 2A and 2B are band diagrams of conventional light-emittingelements;

FIG. 3 illustrates an element structure of a light-emitting elementaccording to an aspect of the present invention;

FIGS. 4A and 4B illustrate illumination devices using a light-emittingelement according to an aspect of the present invention;

FIGS. 5A to 5C illustrate electronic devices using a light-emittingdevice according to an aspect of the present invention;

FIGS. 6A and 6B are graphs showing characteristics of light-emittingelements formed in Example 2;

FIG. 7 is a graph showing characteristics of light-emitting elementsformed in Example 2;

FIG. 8 is a graph showing emission spectra of light-emitting elementsformed in Example 2;

FIG. 9 is a graph showing luminance degradation curves of light-emittingelements formed in Example 2;

FIGS. 10A and 10B are graphs showing characteristics of a light-emittingelement formed in Example 3;

FIG. 11 is a graph showing characteristics of a light-emitting elementformed in Example 3;

FIG. 12 is a graph showing emission spectrum of a light-emitting elementformed in Example 3;

FIG. 13 is a graph showing a luminance degradation curve of alight-emitting element formed in Example 2;

FIGS. 14A and 14B are graphs showing characteristics of light-emittingelements formed in Example 4;

FIG. 15 is a graph showing characteristics of light-emitting elementsformed in Example 4;

FIG. 16 is a graph showing emission spectra of light-emitting elementsformed in Example 4;

FIG. 17 is a graph showing luminance degradation curves oflight-emitting elements formed in Example 4;

FIGS. 18A and 18B are graphs showing characteristics of light-emittingelements formed in Example 5;

FIG. 19 is a graph showing characteristics of light-emitting elementsformed in Example 5;

FIG. 20 is a graph showing emission spectra of light-emitting elementsformed in Example 5;

FIG. 21 is a graph showing luminance degradation curves oflight-emitting elements formed in Example 5;

FIGS. 22A and 22B are graphs showing characteristics of light-emittingelements formed in Example 6;

FIG. 23 is a graph showing characteristics of light-emitting elementsformed in Example 6;

FIG. 24 is a graph showing emission spectrum of light-emitting elementsformed in Example 6;

FIG. 25 is a graph showing luminance degradation curves oflight-emitting elements formed in Example 6;

FIGS. 26A and 26B are graphs showing characteristics of light-emittingelements formed in Example 7;

FIG. 27 is a graph showing characteristics of light-emitting elementsformed in Example 7;

FIG. 28 is a graph showing emission spectra of light-emitting elementsformed in Example 7;

FIG. 29 is a graph showing luminance degradation curves oflight-emitting elements formed in Example 7;

FIG. 30 is a graph showing a CV curve obtained by measurement in Example1;

FIGS. 31A and 31B illustrate a light-emitting device using alight-emitting element according to an aspect of the present invention;

FIGS. 32A and 32B illustrate a light-emitting device using alight-emitting element according to an aspect of the present invention;

FIGS. 33A and 33B are graphs showing characteristics of light-emittingelements formed in Example 8;

FIG. 34 is a graph showing characteristics of light-emitting elementsformed in Example 8;

FIG. 35 is a graph showing emission spectra of light-emitting elementsformed in Example 8; and

FIG. 36 is a graph showing luminance degradation curves oflight-emitting elements formed in Example 8.

BEST MODE FOR CARRYING OUT THE INVENTION

Embodiment modes of the present invention will now be described withreference to the drawings in detail. However, the present invention isnot limited to the following description and it is easily understood bythose skilled in the art that the mode and details can be variouslychanged without departing from the scope and spirit of the presentinvention. Therefore, the present invention is not construed as beinglimited to the description of the embodiment modes shown below.

Embodiment Mode 1

Embodiment Mode 1 will describe a concept of a light-emitting element ofthe present invention. Note that in this specification, “the HOMO levelor the LUMO level is deep” means that the energy level is low, and “theHOMO level or the LUMO level is shallow” means that the energy level ishigh. For example, a substance A having a LUMO level of −2.54 eV has theLUMO level which is deeper by 0.26 eV than a substance having a LUMOlevel of −2.28 eV, and the LUMO level which is shallower by 0.31 eV thana substance C having a LUMO level of −2.85 eV.

Recently, the present inventors have focused on phosphorescent compoundsfor the sake of high performance of light-emitting elements and examineda wide variety of phosphorescent organometallic complexes. As one resultthereof, the present inventors have found that an organometallic complexwhich has a ligand of a pyrazine skeleton and whose central metalbelongs to Group 9 or 10 (hereinafter, referred to a pyrazine-basedorganometallic complex) emits phosphorescence with much higherefficiency as compared to known phosphorescent organometallic complexes.

The property evaluation made by the present inventors found that, ascompared with a general host material (a material used to disperse alight-emitting substance in a light-emitting layer), the pyrazine-basedorganometallic complex has a relatively deep LUMO level (i.e., it hasrelatively high level of an electron-trapping property). On the otherhand, a conventional organometallic complex having a pyridine derivativeas a ligand (hereinafter, a pyridine-based organometallic complex), suchas Ir(ppy)₃ or [btp₂Ir(acac)], has a high hole trapping property becauseit has a shallow HOMO level, but is difficult to trap electrons. Inother words, it is found that pyrazine-based organometallic complexesand pyridine-based organometallic complexes have opposite properties interms of affinity to holes and electrons. Note that this point will bedescribed in Example 1.

The present inventors have found out that the electron-trapping propertyof the pyrazine-based organometallic complexes causes disadvantages aswell as advantages in manufacturing light-emitting elements, from alarge number of experiment results.

One of the advantages is that, as compared with conventionalpyridine-based organometallic complexes, pyrazine-based organometalliccomplexes have hole accepting properties as well as electron acceptingproperties. In other words, when a pyrazine-based organometallic complexis dispersed in a host material of a light-emitting layer, carriers areeasily recombined directly in the pyrazine-based organometallic complex.Therefore, it is not so necessary to pay attention to the efficiency ofenergy transfer from the host material, and thus high efficiencyemission can be achieved.

However, in terms of the carrier balance in the light-emitting layer, itis extremely difficult to select a host material suitable for thepyrazine-based organometallic complex, which is a disadvantage. Thisproblem is described with reference to FIGS. 2A and 2B.

FIGS. 2A and 2B are each a band diagram in the case where alight-emitting layer 200 in which a pyrazine-based organometalliccomplex is dispersed in a host material is sandwiched by ahole-transporting layer 201 and an electron-transporting layer 202. FIG.2A is a band diagram in the case where a first organic compound having ahole-transporting property is used as the host material and FIG. 2B is aband diagram in the case where a second organic compound having anelectron-transporting property is used as the host material.

In FIG. 2A, electrons are trapped by a LUMO level 232, since the LUMOlevel 232 of the pyrazine-based organometallic complex is relativelydeep. Even if electrons are injected into a LUMO level 212 of the firstorganic compound, electrons moves very slowly because the first organiccompound has a hole-transporting property. On the other hand, holes aretransported through the HOMO level 211 of the first organic compound andto the vicinity of the interface with the electron-transporting layer202, since the first organic compound has a hole-transporting property,and a HOMO level 231 of the pyrazine-based organometallic complex doesnot hinder holes (i.e., does not form a deep trap). In other words, alight-emitting region is limited to an extremely narrow area which is aninterface between the light-emitting layer 200 and theelectron-transporting layer 202.

If the electron-transporting layer 202 has a low hole blocking property,holes may reach the electron-transporting layer 202 depending oncombination of materials as illustrated in FIG. 2A. Thus, theelectron-transporting layer 202 emits light, thereby drasticallyreducing the emission efficiency of the light-emitting element. Needlessto say, the present inventors have confirmed that the problem is solvedwhen a highly hole-blocking substance is used for theelectron-transporting layer 202, and high emission efficiency can beachieved; however, the lifetime is adversely affected, as describedabove. Further, there is a concern about reduction in efficiency on thehigh luminance side due to the triplet-triplet extinction.

Next, in FIG. 2B, since the pyrazine-based organometallic complex has arelatively deep LUMO level 232, electrons are trapped by the LUMO level232. Since the second organic compound has an electron-transportingproperty, some electrons are trapped, but some electrons are transportedthrough a LUMO level 222 of the second organic compound and to thehole-transporting layer 201 little by little. Note that the mobility islower than the original electron mobility of the second organiccompound. On the other hand, since the second organic compound has anelectron-transporting property, the HOMO level 221 is relatively deepand holes are difficult to be injected. Even if holes are injected, themobility of the holes is extremely low, since the first organic compoundhas an electron-transporting property. There may be a case where holesare injected in the HOMO level 231 of the pyrazine-based organometalliccomplex, but the transporting ability is small. In other words, in thestructure of FIG. 2B, the light-emitting layer 200 has normally anelectron-transporting property; however, electrons are difficult to movedue to the trapping. On the other hand, holes are accumulated at theinterface between the hole-transporting layer 201 and the light-emittinglayer 200.

In this case, the hole density is extremely high at the interfacebetween the light-emitting layer 200 and the hole-transporting layer 201but is extremely low in the other regions. On the other hand, electronsspread across the whole region of the light-emitting layer 200 due tothe trapping, but the electron density is low as a whole. In otherwords, the hole distribution and the electron distribution are differentfrom each other in terms of the density and the distribution profile.Therefore, it becomes difficult to recombine holes and electrons in abalanced manner and achieve the high emission efficiency. In addition,this imbalance causes an adverse affect on the lifetime.

In view of the above problems, the present inventors have thought thatthe following points are important. In other words, the first point isthat a certain large amount of holes are allowed to be injected into thelight-emitting layer 200 in the structure of FIG. 2B. The second pointis that holes injected into the light-emitting layer 200 move toward theelectron-transporting layer 202 little by little, so that the balancewith electrons which move slowly can be obtained in the structure ofFIG. 2B. The structure to fulfill these two points is a structure of thepresent invention, which is typified by a band diagram as illustrated inFIG. 1.

A light-emitting layer 100 in FIG. 1 includes a first organic compoundhaving a hole-transporting property, a second organic compound having anelectron-transporting property and a pyrazine-based organometalliccomplex. Since a LUMO level 132 of the pyrazine-based organometalliccomplex is lower than a LUMO level 112 of the first organic compound anda LUMO level 122 of the second organic compound, electrons are trappedby the LUMO level 132 of the pyrazine-based organometallic complex. Notethat some electrons move toward a hole-transporting layer 101 sidelittle by little without being trapped whereas some electrons aretrapped by the LUMO level 132 of the pyrazine-based organometalliccomplex since the second organic compound has an electron-transportingproperty. On the other hand, since the first organic compound has ahole-transporting property and also a hole accepting property, holes areinjected into the HOMO level 111 of the first organic compound first.Holes are difficult to be injected to the HOMO level 121 of the secondorganic compound. In this case, the amount of the first organic compoundis adjusted to control the mobility of the injected holes, so that itcan be balanced with the mobility of electrons coming from theelectron-transporting layer 102. In other words, in the light-emittinglayer 100, the balance between holes and electrons can be good. Then,holes are injected into the HOMO level 131 of the pyrazine-basedorganometallic complex and are recombined with trapped electrons to emitlight.

By exercising such an ingenuity, the present inventors have found outthat the potential of pyrazine-based organometallic complexes, which ishigh emission efficiency, can be utilized to the maximum. To oursurprise, the present inventors have also found out that the structureillustrated in FIG. 1 of the present invention can achieve several timesto dozen of times long lifetime of the structures in FIGS. 2A and 2B.The first organic compound and the second organic compound are used forhosts in FIGS. 2A and 2B respectively. In FIG. 1, two types of organiccompounds, the first organic compound and the second organic compoundare used for a host. This point is different from FIGS. 2A and 2B. Thephenomenon that the lifetime is extremely longer just because of thatpoint cannot be seen in general, and is our surprise.

Patent Document 1 also describes that longer lifetime can be achieved byusing a mixed layer for a light-emitting layer, and it is at highest twotimes improvement. Patent Document 1 cannot obtain as good improvementin lifetime as the present invention. According to Patent Document 1,the charge accumulation which leads to degradation of organic materialsseems to be reduced by the mixed layer. However, Patent Document 1 doesnot appear to refer to the problem of carrier balance caused by theelectron-trapping property of pyrazine-based organometallic complexes.In other words, Patent Document 1 uses a different organometalliccomplex from the present invention. Thus, it is thought that theprinciple and effect in the case where two types of host materials areused are also different, which leads to the difference in theimprovement of lifetime. A phosphorescent compound employed in PatentDocument 1 is PtOEP, which is a porphyrin complex, and a pyridine-basedorganometallic complex [btp₂Ir(acac)], and they are both have lowelectron-trapping properties and high hole trapping properties. In otherwords, the compounds have properties opposite to pyrazine-basedorganometallic complexes of the present invention.

The conception and effect of the present invention has been describedabove with reference the band diagrams. Hereinafter, a more specificstructure will be described.

Embodiment Mode 2

Embodiment Mode 2 will cite specific materials which can be used for astructure of a light-emitting element according to the presentinvention. FIG. 3 illustrates a structure of a light-emitting element.

FIG. 3 illustrates a light-emitting element of the present invention.The light-emitting element includes a light-emitting layer 313 between afirst electrode 301 serving as anode and a second electrode 302 servingas a cathode, and the light-emitting layer 313 includes a first organiccompound 321 having a hole-transporting property, a second organiccompound 322 having an electron-transporting property and apyrazine-based organometallic complex 323. A structure of thelight-emitting layer 313 is described below.

In the light-emitting layer 313, the first organic compound 321 is acompound having a hole-transporting property. Specifically, an aromaticamine compound such as 4,4′-bis[N-(1-napthyl)-N-phenylamino]biphenyl(abbreviation: NPB), 4,4′-bis[N-(9-phenanthryl)-N-phenylamino]biphenyl(abbreviation: PPB), 4,4′-bis[N-(3-methylphenyl)-N-phenylamino]biphenyl(abbreviation: TPD),4,4′-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl(abbreviation: DFLDPBi), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine(abbreviation: TDATA),4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine(abbreviation: m-MTDATA), 4,4′,4″-tri(N-carbazolyl)triphenylamine(abbreviation: TCTA), 1,1-bis[4-(diphenylamino)phenyl]cyclohexane(abbreviation: TPAC), 9,9-bis[4-(diphenylamino)phenyl]fluorene(abbreviation: TPAF),4-(9-carbazolyl)-4′-(5-phenyl-1,3,4-oxadiazol-2-yl)triphenylamine(abbreviation: YGAO11), orN-[4-(9-carbazolyl)phenyl]-N-phenyl-9,9-dimethylfluoren-2-amine(abbreviation: YGAF) can be used. Also, a carbazole derivative such as4,4′-di(N-carbazolyl)biphenyl (abbreviation: CBP),1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), or1,3,5-tris(N-carbazolyl)benzene (abbreviation: TCzB) can be used.Further, a high molecular compound such as poly(4-vinyltriphenylamine)(abbreviation: PVTPA) can also be used as such an aromatic aminecompound. As a carbazole derivative, a high molecular compound such aspoly(N-vinylcarbazole) (abbreviation: PVK) can also be used. The tripletexcitation energy of the first organic compound 321 as described aboveis preferably larger than that of the pyrazine-based organometalliccomplex 323.

On the other hand, the second organic compound 322 is a compound havingan electron-transporting property. Specifically, a heteroaromaticcompound such as 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]carbazole(abbreviation: CO11),1,3-bis[5-(p-tert-buthylphenyl)-1,3,4-oxadiazol-2-yl]benzene(abbreviation: OXD-7),2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation:PBD), 2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole)(abbreviation: TPBI),3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole(abbreviation: TAZ),3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole(abbreviation: p-EtTAZ),9,9′,9″-[1,3,5-triazine-2,4,6-triyl]tricarbazole (abbreviation: TCzTRZ),2,2′,2″-(1,3,5-benzenetriyl)tris(6,7-dimethyl-3-phenylquinoxaline)(abbreviation: TriMeQn),9,9′-(quinoxaline-2,3-diyldi-4,1-phenylene)di(9H-carbazole)(abbreviation CzQn),3,3′,6,6′-tetraphenyl-9,9′-(quinoxaline-2,3-diyldi-4,1phenylene)di(9H-carbazole)(abbreviation: DCzPQ), bathophenanthroline (abbreviation: BPhen), orbathocuproine (abbreviation: BCP) can be used. A metal complex such asis bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III)(abbreviation: BAlq),tris[2-(2-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazolato]aluminum(III)(abbreviation: Al(OXD)₃),tris(2-hydroxyphenyl-1-phenyl-1H-benzimidazolato)aluminum(III)(abbreviation: Al(BIZ)₃),bis[2-(2-hydroxyphenyl)benzothiazolato]zinc(II) (abbreviation:Zn(BTZ)₂), or bis[2-(2-hydroxyphenyl)benzoxazolato]zinc(II)(abbreviation: Zn(PBO)₂) can be used. Further, a high molecular compoundsuch as poly(2,5-pyridine-diyl) (abbreviation: PPy) can also be used assuch a heteroaromatic compound. As a metal complex, metal complex highmolecular compounds disclosed as in the following reference can also beused (TAO et al., C—H BOND ACTIVATION BY A FERRIC METHOXIDE COMPLEX:MODELING THE RATE-DETERMINING STEP IN THE MECHANISM OF LIPOXYGENASE,APPL. PHYS. LETT. (APPLIED PHYSICS LETTERS, vol. 70, No. 12, 24 Mar.1997, pages 1503-1505.). Note that the triplet excitation energy of thesecond organic compound 322 as described above is preferably larger thanthat of the pyrazine-based organometallic complex 323.

The pyrazine-based organometallic complex 323 is an organometalliccomplex which has a ligand having a pyrazine skeleton, and whose acentral metal is an element belonging to Group 9 (Co, Rh, Ir) or anelement belonging to Group 10 (Ni, Pd, Pt). Further, the organometalliccomplex has a property of emitting phosphorescence. A specific structureof this pyrazine-based organometallic complex will be described inEmbodiment Mode 3.

As described above, the first organic compound, the second organiccompound and the pyrazine-based organometallic complex are combinedsuitably to constitute a light-emitting layer of a light-emittingelement of the present invention. Note that the light-emitting layer mayinclude another substance.

In the light-emitting layer, preferably, at least one of the firstorganic compound and the second organic compound serves as a hostmaterial and the pyrazine-based organometallic complex serves as a guestmaterial. This is in order to prevent concentration quenching of thepyrazine-based organometallic complex. Also, this is in order that thecarrier balance in the light-emitting layer can be adjusted by the firstorganic compound and the second organic compound.

Therefore, in the light-emitting element of the present invention,preferably, the amount of the first organic compound and/or the secondorganic compound is larger than that of the pyrazine-basedorganometallic complex. Specifically, its volume fraction or its massfraction is preferably high. In addition, in terms of prevention ofconcentration quenching, the ratio of the pyrazine-based organometalliccomplex to the light-emitting layer is preferably 1 mass % to 10 mass %,inclusive.

In the light-emitting layer, the mass ratio of the first organiccompound to the second organic compound is preferably in the range of1:20 to 20:1. In other words, the mass ratio of the second organiccompound to the first organic compound is preferably 1/20 to 20,inclusive. The light-emitting element having the first and secondcompounds whose mass ratio are not within the range can be substantiallythe same as the state of FIG. 2A or 2B described above, if.

The present inventors have found that the structure of thelight-emitting layer in which the amount of the second organic compoundhaving an electron-transporting property is equal to or higher than thatof the first organic compound having a hole-transporting property isextremely effective. This appears to be caused from that the holemobility is higher than the electron mobility in general organiccompounds. Accordingly, in the present invention, the mass ratio of thesecond organic compound to the first organic compound is more preferably1 to 20, inclusive. The range which is extremely effective for obtaininglong lifetime is 5 to 20, inclusive, in particular.

The electron-trapping property of the pyrazine-based organometalliccomplex used in the present invention is often deeper than the LUMOlevel of the first organic compound and the LUMO level of the secondorganic compound by 0.2 eV or more, specifically. In such a case, thelifetime improvement and the efficiency improvement are significant, andthus one feature of the present invention is that the LUMO level of thepyrazine-based organometallic complex is deeper than the LUMO level ofthe first organic compound and the LUMO level of the second organiccompound by 0.2 eV or more.

Next, layers other than the light-emitting layer 313 are described. Ahole-transporting layer 312 and a hole-injecting layer 311 are notnecessarily provided, and they may be provided as necessary. Specificmaterials for forming these layers are preferably hole-transportingcompounds, and NPB, PPB, TPD, DFLDPBi, TDATA, m-MTDATA, TCTA, TPAC,TPAF, YGAO11, YGAF, CBP, mCP, TCzB, PVTPA, PVK or the like as describedabove can be used. An anthracene derivative having a low tripletexcitation energy such as 9,10-bis[4-(diphenylamino)phenyl]anthracene(abbreviation: TPA2A) or 2-tert-butyl-9,10-di(2-naphthyl)anthracene(abbreviation: t-BuDNA) can also be used. The present invention is alsocharacterized that an anthracene derivative having a low tripletexcitation energy is applied to the hole-transporting layer 312 and thehole-injecting layer 311.

This feature can be explained as below. The light-emitting layer 313 ofthe present invention has a good carrier balance as described inEmbodiment Mode 1, and a light-emitting region does not exist close tothe interface between the light-emitting layer 313 and thehole-transporting layer 312. Therefore, if a substance having a lowertriplet excitation energy than the pyrazine-based organometallic complex323 is applied to the hole-transporting layer 312, the substance isdifficult to serve as a quencher to the pyrazine-based organometalliccomplex 323.

The hole-transporting layer 312 or the hole-injecting layer 311 may beformed by mixing the above hole-transporting compound and an electronacceptor. As the electron acceptor, in addition to an organic compoundsuch as chloranil or7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation:F₄-TCNQ), transition metal oxide such as molybdenum oxide, vanadiumoxide, or rhenium oxide can be used. In particular, as thehole-injecting layer 311, an organic compound such as copperphthalocyanine, vanadyl phthalocyanine, or fluorocarbon, or an inorganiccompound such as molybdenum oxide, ruthenium oxide, or aluminum oxidecan also be used. The hole-injecting layer 311 may have a multilayerstructure formed by stacking two or more layers. Further, thehole-injecting layer 311 and the hole-transporting layer 312 may beformed by mixing two or more kinds of substances.

The electron-transporting layer 314 and the electron-injecting layer 315are not necessarily required, and may be provided as necessary. As aspecific material which forms these layers, an electron-transportingcompound is preferable. The above-described CO11, OXD-7, PBD, TPBI, TAZ,p-EtTAZ, TCzTRZ, TriMeQn, CzQn, DCzPQ, BPhen, BCP, BAlq, Al(OXD)₃,Al(BIZ)₃, Zn(BTZ)₂, Zn (PBO)₂, PPy, or the like can be used. A substancehaving a low triplet excitation energy such astris(8-quinolinolato)aluminum(III) (abbreviation: Alq₃),tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation Almq₃), orbis(10-hydroxybenzo[h]quinolinato)berylium(II) (abbreviation: BeBq₂) canbe used (for example, it is reported that the phosphorescence spectrumof Alq₃ is about 650 to 700 mm of deep red). The present invention isalso characterized that a substance having a low triplet excitationenergy is applied as the electron-transporting layer 314 and theelectron-injecting layer 315.

This feature can be explained as below. The light-emitting layer 313 ofthe present invention has a good carrier balance as described inEmbodiment Mode 1, and a light-emitting region does not exist close tothe interface between the light-emitting layer 313 and theelectron-transporting layer 314. Therefore, even if a substance having alower triplet excitation energy than the pyrazine-based organometalliccomplex 323 is applied to the electron-transporting layer 314, thesubstance is difficult to serve as a quencher to the pyrazine-basedorganometallic complex 323.

The electron-transporting layer 314 and the electron-injecting layer 315may be formed by mixing the above-described electron-transportingcompounds and an electron donor. As the electron donor, in addition toan organic compound such as tetrathiafulvalene, alkali metal such aslithium or cesium, alkaline earth metal such as magnesium or calcium,rare-earth metal such as erbium or ytterbium, or an oxide of thesemetals can be used. In particular, as the electron-injecting layer 315,an alkali metal compound, an alkaline earth metal compound, or arare-earth metal compound, such as lithium oxide, lithium fluoride,calcium fluoride, erbium fluoride, can be used alone. Theelectron-injecting layer 315 may have a multilayer structure formed bystacking two or more layers. Further, the electron-transporting layer314 and the electron-injecting layer 315 may be formed by mixing two ormore kinds of substances.

Although the first electrode 301 is not limited in particular, asdescribed in Embodiment Mode 2, the first electrode 301 is preferablyformed using a substance with high work function when the firstelectrode 301 serves as an anode. Specifically, in addition to indiumtin oxide (ITO), indium tin oxide containing silicon oxide (ITSO), orindium oxide containing 2 to 20 wt % zinc oxide (IZO), gold (Au),platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum(Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), or the likecan be used. The first electrode 301 can be formed by, for example, asputtering method, an evaporation method, or the like.

Although the second electrode 302 is not limited in particular, asdescribed in Embodiment Mode 2, the second electrode 302 is preferablyformed using a substance with low work function when the secondelectrode 302 serves as a cathode. Specifically, in addition to aluminum(Al) or indium (In), alkali metal such as lithium (Li) or cesium (Cs),alkaline earth metal such as magnesium (Mg) or calcium (Ca), orrare-earth metal such as erbium (Er) or ytterbium (Yb) can be used. Inaddition, alloy such as aluminum-lithium alloy (AlLi) ormagnesium-silver alloy (MgAg) can also be used. In addition, when theelectron-transporting compound and an electron donor are combined toform the electron-injecting layer 315, a highly light-transmittingsubstance having a high work function can be used. The second electrode302 can be formed by, for example, a sputtering method, an evaporationmethod, or the like.

In order to extract generated light to the outside, it is preferablethat one or both of the first electrode 301 and the second electrode 302be an electrode formed of a highly light-transmitting substance, such asITO, ITSO, or IZO. Alternatively, one or both of the first electrode 301and the second electrode 302 is preferably an electrode formed to have athickness of several to several tens of nanometers so that visible lightcan be transmitted.

In the light-emitting element of the present invention described above,each of the hole-injecting layer 311, the hole-transporting layer 312,the light-emitting layer 313, the electron-transporting layer 314, andthe electron-injecting layer 315 may be formed by any method such as anevaporation method, an ink-jet method, or a coating method. The firstelectrode 301 or the second electrode 302 may also be formed by anymethod such as a sputtering method, an evaporation method, an ink-jetmethod, or a coating method.

The above-described light-emitting element of the present invention maybe applied to a tandem type light-emitting element (also referred to asa multiphoton element).

Embodiment Mode 3

Embodiment Mode 3 will specifically describe a structure of apyrazine-based organometallic complex which can be used for alight-emitting element of the present invention.

The pyrazine-based organometallic complex is an organometallic complexwhich has a ligand having a pyrazine skeleton, and whose a central metalis an element belonging to Group 9 (Co, Rh, Ir) or an element belongingto Group 10 (Ni, Pd, Pt). Further, the organometallic complex may have aproperty of emitting phosphorescence.

Many of organometallic complexes belonging to Group 9 or 10 exhibit MLCT(Metal to Ligand Charge Transfer) transition. In particular, the tripletMLCT transition is often observed in phosphorescent compounds. The LUMOlevel of the organometallic complex exhibiting MLCT transition isdetermined by the rank of the LUMO level of a ligand. Thus, if a ligandhaving a high LUMO level is used, the LUMO level of the organometalliccomplex is also high, and if a ligand having a low LUMO level, the LUMOlevel of the organometallic complex is also low. Pyrazine has a LUMOlevel lower than pyridine, and thus, a pyrazine-based organometalliccomplex of the present invention exhibits a LUMO level lower (i.e., ahigher electron-trapping property) than a conventional pyridine-basedorganometallic complex.

A ligand of the pyrazine-based organometallic complex used in thepresent invention may have a pyrazine skeleton. In particular, when theligand is a 2-arylpyrazine derivative, the ligand can be cyclometalatedto the central metal. The cyclometalated complex can realize a highphosphorescence quantum yield. Therefore, the ligand is preferably a2-arylpyrazine derivative.

As an organometallic complex whose 2-arylpyrazine derivative iscyclometalated, an organometallic complex typified by the followinggeneral formula (G1) is given.

In the formula, A_(r) represents an arylene group. R¹ represents eitheran alkyl group or an aryl group. R² represents hydrogen, an alkyl groupor an aryl group. R³ represents either hydrogen or an alkyl group. Inaddition, R² and R³ may be bound to each other to form an alicycle. Inaddition, M is a central metal, and represents either an elementbelonging to Group 9 or an element belonging to Group 10.

Further, when a 2-phenylpyrazine derivative which is a kind of2-arylpyrazine derivatives is a ligand, the ligand can beortho-metalated to the central metal (ortho-metalation is a kind ofcyclometalation). The present inventors have found that such anortho-metal complex in which 2-phenylpyrazine is ortho-metalated canrealize particularly high phosphorescence quantum yield. Therefore, apreferred mode of the ligand is a 2-phenylpyrazine derivative.

As an organometallic complex in which a 2-phenylpyrazine derivative isortho-metalated, an organometallic complex having a structurerepresented by the following general formula (G2) is given.

In the formula, R¹ represents either an alkyl group or an aryl group. R²represents hydrogen, an alkyl group or a phenyl group. R³ representseither hydrogen or an alkyl group. In addition, R² and R³ may be boundto each other to form an alicycle. R⁴ to R⁷ represent any of hydrogen,an alkyl group, a halogen group, a haloalkyl group, an alkoxy group, andan alkoxycarbonyl group. In addition, M is a central metal, andrepresents either an element belonging to Group 9 or an elementbelonging to Group 10.

Among organometallic complexes in which a 2-phenylpyrazine derivative isortho-metalated, an organometallic complex in which a2,5-diphenylpyrazine derivative is ortho-metalated has a still deeperLUMO level. Therefore, when a ligand is a 2,5-diphenylpyrazinederivative, the effect of a light-emitting element of the presentinvention is remarkable, which is preferable.

As an organometallic complex in which a 2,5-diphenylpyrazine derivativeis ortho-metalated, an organometallic complex having the followinggeneral formula (G3) is given.

In the formula, R¹ represents either an alkyl group or a phenyl group.R³ represents either hydrogen or an alkyl group. R⁴ to R¹² represent anyof hydrogen, an alkyl group, a halogen group, a haloalkyl group, analkoxy group, and an alkoxycarbonyl group. In addition, M is a centralmetal, and represents either an element belonging to Group 9 or anelement belonging to Group 10.

Specifically, the organometallic complexes having structures representedby the general formulae (G1) to (G3) are preferably mixed ligandorganometallic complexes having a ligand L represented by the generalformulae (G4) to (G6) other than the pyrazine derivative. This isbecause such complexes are easy to be synthesized.

In the formula, A_(r) represents an arylene group. R¹ represents eitheran alkyl group or an aryl group. R² represents hydrogen, an alkyl groupor an aryl group. R³ represents either hydrogen or an alkyl group. Inaddition, R² and R³ may be bound to each other to form an alicycle. Inaddition, M is a central metal, and represents either an elementbelonging to Group 9 or an element belonging to Group 10. L is amonoanionic ligand. When the M is an element belonging to Group 9, n is2 (n=2) and when the M is an element belonging to Group 10, n is 1(n=1).

In the formula, R¹ represents either an alkyl group or a phenyl group.R² represents hydrogen, an alkyl group or a phenyl group. R³ representseither hydrogen or an alkyl group. In addition, R² and R³ may be boundto each other to form an alicycle. R⁴ to R⁷ represent any of hydrogen,an alkyl group, a halogen group, a haloalkyl group, an alkoxy group, andan alkoxycarbonyl group. In addition, M is a central metal, andrepresents either an element belonging to Group 9 or an elementbelonging to Group 10. L is a monoanionic ligand. When the M is anelement belonging to Group 9, n is 2 (n=2) and when the M is an elementbelonging to Group 10, n is 1 (n=1).

In the formula, R¹ represents either an alkyl group or a phenyl group.R³ represents either hydrogen or an alkyl group. R⁴ to R¹² represent anyof hydrogen, an alkyl group, a halogen group, a haloalkyl group, analkoxy group, and an alkoxycarbonyl group. In addition, M is a centralmetal, and represents either an element belonging to Group 9 or anelement belonging to Group 10. L is a monoanionic ligand. When the M isan element belonging to Group 9, n is 2 (n=2) and when the M is anelement belonging to Group 10, n is 1 (n=1).

The central metal of the above pyrazine-based organometallic complex ispreferably iridium or platinum in terms of heavy atom effect. Inparticular, iridium is preferable since iridium can provide remarkableheavy atom effect, extremely high efficiency and is chemically stable.

Next, the arylene group A_(r), each subsistent R¹ to R¹², and themonoanionic ligand L in the above general formulae (G1) to (G6) aredescribed in detail.

As the arylene group A_(r), an arylene group having 6 to 25 carbon atomsis preferably used, specifically, phenylenes, julolidilenes,naphtylenes, spirofluorene-diyls, 9,9-dimethylfluoren-diyls,9,9-dialkylfluonren-diyls can be applied. Further, these arylene groupsA_(r) may have a substituent. As the substituent at that time, an alkylgroup, a halogen group, a haloalkyl group, an alkoxy group, analkoxycarbonyl group or the like can be used.

Next, R¹ represents either an alkyl group or a phenyl group. Further,the phenyl group may have a substituent. As the substituent at thattime, an alkyl group, a halogen group, a haloalkyl group, an alkoxygroup, an alkoxycarbonyl group or the like can be used.

R² represents hydrogen, an alkyl group or a phenyl group. Further, thephenyl group may have a substituent. As the substituent at that time, analkyl group, a halogen group, a haloalkyl group, an alkoxy group, analkoxycarbonyl group or the like can be used.

R³ represents hydrogen or an alkyl group. In addition, R² and R³ may bebound to each other to form an alicycle. Specifically, R² and R³ arebound to each other to form a 1,4-butylenes group.

R⁴ to R¹² represent hydrogen, an alkyl group, a halogen group, ahaloalkyl group, an alkoxy group, or an alkoxycarbonyl group.

In the above structure, the alkyl group preferably has 1 to 4 carbonatoms, specifically, a methyl group, an ethyl group, an isopropyl group,a t-butyl group or the like can be given. In addition, a fluoro group,and a chloro group are nominated for a halogen group, and a fluoro groupis preferable in terms of chemical stability. As the haloalkyl group, atrifluoromethyl group is preferable. Further, the alkoxy grouppreferably has 1 to 4 carbon atoms, specifically, a methoxy group, anethoxy group, an isopropoxy group, and a t-butoxy group are given. Inaddition, the alkoxycarbonyl group preferably has 2 to 5 carbon atoms,and specifically, a methoxycarbonyl group, an ethoxycarbonyl group, anisopropoxy carbonyl group, and a t-butoxycarbonyl group are nominatedfor the alkoxycarbonyl group.

Next, the monoanionic ligand L will be described. The monoanionic ligandL is preferably a monoanionic bidentate chelate ligand having aβ-diketone structure, a monoanionic bidentate chelate ligand having acarboxyl group, a monoanionic bidentate chelate ligand having a phenolichydroxyl group, or a monoanionic bidentate chelate ligand in which twoligand elements are both nitrogen, since they have a high coordinativeability. More specifically, monoanionic ligands represented by thefollowing structural formulae (L1) to (L8) are given. However, themonoanionic ligand L is not limited to these ligands.

From the above described modes, pyrazine-based organometallic complexeswhich can be used in the present invention are structured. Specificstructural formulae are given below (the structural formulae (1) to(17)). Note that the pyrazine-based organometallic complex of thepresent invention is not limited to these complexes.

Embodiment Mode 4

Embodiment Mode 4 will explain an image display device as an example oflight-emitting device having a light-emitting element of the presentinvention.

This embodiment mode will describe an image display device having alight-emitting element of the present invention in a pixel portion, withreference to FIGS. 31A and 31B. FIG. 31A is a top view illustrating alight-emitting device while FIG. 31B is a cross-sectional view takenalong the lines A-A′ and B-B′ of FIG. 31A. This image display deviceincludes a driver circuit portion (source side driver circuit) 601 shownwith a dotted line; a pixel portion 602 shown with a dotted line; and adriver circuit portion (gate side driver circuit) 603 shown with adotted line, to control emission of the light-emitting element.Moreover, a reference numeral 604 denotes a sealing substrate; 605, asealing material; and 607, a space surrounded by the sealing material605.

A leading wiring 608 is provided to transmit a signal to be inputted tothe source side driver circuit 601 and the gate side driver circuit 603,and receive a video signal, a clock signal, a start signal, a resetsignal, and the like from an FPC (Flexible Printed Circuit) 609, whichserves as an external input terminal. Although only the FPC isillustrated here, the FPC may be provided with a printed wiring board(PWB). The light-emitting device in this specification includes not onlya light-emitting device itself but also a light-emitting device has anFPC or a PWB attached thereto.

Next, the cross-sectional structure is described with reference to FIG.31B. Over an element substrate 610 are formed the driver circuit portionand the pixel portion. Here, the source side driver circuit 601, whichis the driver circuit portion, and one pixel in the pixel portion 602are shown.

In the source side driver circuit 601, a CMOS circuit in which ann-channel TFT 623 and a p-channel TFT 624 are combined is formed. Such adriver circuit may be formed by using various circuits such as a CMOScircuit, a PMOS circuit, or an NMOS circuit. Although this embodimentmode illustrates a driver-integrated type where the driver circuit isformed over the substrate, the present invention is not restricted tothis, and the driver circuit may be formed outside the substrate, notover the substrate.

The pixel portion 602 includes a plurality of pixels each including aswitching TFT 611, a current control TFT 612, and a first electrode 613electrically connected to a drain of the current control TFT 612. Aninsulator 614 is formed so as to cover an end portion of the firstelectrode 613. Here, the insulator 614 is formed using a positivephotosensitive acrylic resin film.

In order to improve the coverage, an upper end portion or a lower endportion of the insulator 614 is formed so as to have a curved surfacewith curvature. For example, in the case of using a positivephotosensitive acrylic for the insulator 614, only the upper end portionof the insulator 614 preferably has a curved surface with curvature (aradius of curvature of 0.2 to 3 μm). As the insulator 614, either anegative type which becomes insoluble in etchant by irradiation withlight or a positive type which becomes soluble in etchant by irradiationwith light can be used.

Over the first electrode 613, a layer 616 including a light-emittinglayer and a second electrode 617 are formed. Here, the first electrode613 can be formed with various metals, alloys, electrically conductivecompounds, or mixture thereof. When the first electrode is used as ananode, it is preferable to use, among those materials, a metal, analloy, an electrically conductive compound or a mixture thereof having ahigh work function (work function of 4.0 eV or higher), or the like. Forexample, a single layer of indium tin oxide containing silicon, indiumzinc oxide (IZO), a titanium nitride film, a chromium film, a tungstenfilm, a Zn film, a Pt film, or the like can be used. Moreover, amultilayer including a titanium nitride film and a film containingaluminum as its main component; a three-layer structure including atitanium nitride film, a film containing aluminum as its main component,and a titanium nitride film; or the like can be used. The multilayerstructure achieves to have low wiring resistance, favorable ohmiccontact, and a function as an anode.

The layer 616 including a light-emitting layer is formed by variousmethods such as an evaporation method using an evaporation mask, aninkjet method, a spin coating method, or the like. The layer 616including a light-emitting layer has the light-emitting layer describedin Embodiment Mode 1 to Embodiment Mode 3. As another material for thelayer 616 including a light-emitting layer, a low molecular material, amedium molecular material having an intermediate property between a highmolecular material and a low molecular material (including oligomer anddendrimer), or a high molecular material may be used. As the materialfor the layer including the light-emitting layer, not only an organiccompound but also an inorganic compound may be used.

As the material for the second electrode 617, various types of metals,alloys, electrically conductive compounds, mixtures of these, or thelike can be used. When the second electrode is used as a cathode, amongthem, a metal, alloy, electrically conductive compound, mixture ofthese, or the like each having a low work function (work function of 3.8eV or lower) is preferable. As an example, an element belonging to Group1 or Group 2 in the periodic table, i.e., an alkali metal such aslithium (Li) or cesium (Cs), an alkaline earth metal such as magnesium(Mg), calcium (Ca), or strontium (Sr), or an alloy containing any ofthese (such as Mg:Ag or Al:Li); and the like can be given. In the casewhere light generated in the layer 616 including a light-emitting layeris transmitted through the second electrode 617, the second electrode617 is preferably formed with a multilayer of a metal thin film whosethickness is made thin, and a transparent conductive film (indium tinoxide (ITO), indium tin oxide including silicon or silicon oxide, indiumzinc oxide (IZO), indium oxide containing tungsten oxide and zinc oxide(IWZO), or the like).

When the sealing substrate 604 and the element substrate 610 areattached to each other by the sealing material 605, the light-emittingelement 618 is provided in the space 607 surrounded by the elementsubstrate 610, the sealing substrate 604, and the sealing material 605.The space 607 may be filled with filler, and may be filled with an inertgas (such as nitrogen or argon), the sealing material 605, or the like.

An epoxy-based resin is preferable for the sealing material 605. Thematerial preferably allows as little moisture and oxygen as possible topenetrate. As a material for the sealing substrate 604, a plasticsubstrate made of FRP (Fiberglass-Reinforced Plastics), PVF (polyvinylfluoride), polyester, acrylic, or the like can be used besides a glasssubstrate or a quartz substrate.

In this way, the active matrix image display device having thelight-emitting element of the present invention can be provided.

Although this embodiment mode has described the active matrix type imagedisplay device in which the driving of the light-emitting element iscontrolled by transistors, the image display device may be of a passivetype in which the light-emitting element is driven without particularlyproviding elements for driving, such as transistors. FIG. 32 is aperspective view of a passive type image display device manufactured byapplying the present invention. In FIG. 32, a layer 955 including alight-emitting layer is provided between an electrode 952 and anelectrode 956 over a substrate 951. An end portion of the electrode 952is covered with an insulating layer 953. Then, over the insulating layer953 is provided a partition layer 954. A side wall of the partitionlayer 954 has such a gradient that the distance between one side walland the other side wall becomes shorter as approaching the substratesurface. That is to say, a cross section of the partition layer 954 in ashort-side direction is trapezoid-like, in which a bottom side (a sidein the same direction as a surface direction of the insulating layer953, which is in contact with the insulating layer 953) is shorter thanan upper side (a side in the same direction as the surface direction ofthe insulating layer 953, which is not in contact with the insulatinglayer 953). In this way, by providing the partition layer 954, a problemof defects in a light-emitting element due to electrostatic and the likecan be prevented.

As described above, the image display device of the present inventiondescribed in Embodiment Mode 4 has the light-emitting element of thepresent invention described in Embodiment Modes 1 to 3. Thus, the imagedisplay device has high emission efficiency and long lifetime.Therefore, the image display device using a light-emitting element ofthe present invention consumes low electric power and has a longlifetime.

Embodiment Mode 4 can be freely combined with any of the otherembodiment modes.

Embodiment Mode 5

The light-emitting element of the present invention can be used for anillumination device, which is an example of light-emitting devices,because the light-emitting element of the present invention has highemission efficiency and long lifetime. Embodiment Mode 5 will describean application example of an illumination device using thelight-emitting element of the present invention.

FIG. 4A shows an example of a liquid crystal display device in which thelight-emitting element of the present invention is used as a backlight.The liquid crystal display device illustrated in FIG. 4A includes ahousing 401, a liquid crystal layer 402, a backlight 403, and a housing404, in which the liquid crystal layer 402 is connected to a driver IC405. The backlight 403 uses the light-emitting element of the presentinvention, and current is supplied to the backlight 403 through aterminal 406.

When the light-emitting element of the present invention is used as thebacklight of the liquid crystal display device, the backlight havinghigh emission efficiency and a long lifetime can be obtained. Moreover,since a backlight using the light-emitting element of the presentinvention is an illumination device of surface light emission and can beformed in a large area, the backlight can be made larger and the liquidcrystal display device can also have a larger area. Moreover, since thelight-emitting device is thin and consumes less electric power,reduction in thickness and power consumption of the display device ispossible.

FIG. 4B illustrates an example in which an illumination device using thelight-emitting element of the present invention is used as a lightsource of a desk lamp. The desk lamp illustrated in FIG. 4B includes ahousing 411 and a light source 412. The light-emitting element of thepresent invention is used as the light source 412. Since thelight-emitting element of the present invention has a long lifetime, thedesk lamp can also have a long lifetime.

The illumination device of the present invention described in EmbodimentMode 5 has the light-emitting element of the present invention describedin Embodiment Modes 1 to 3. Thus, the illumination device has highemission efficiency and long lifetime. Therefore, the illuminationdevice using a light-emitting element of the present invention consumeslow electric power and has a long lifetime.

Embodiment Mode 6

An image display device of the present invention, described inEmbodiment Mode 4, can display an excellent image. Therefore, electronicdevices that are capable of providing an excellent image can be obtainedby applying the image display device of the present invention to displayportions of the electronic devices. In addition, the image displaydevice or the illumination device (i.e., a light-emitting device)including the light-emitting element of the present invention consumeslow power and has long life. Therefore, electronic devices with lowpower consumption can be obtained by applying the light-emitting deviceof the present invention to the display portions of the electronicdevices, and for example, a telephone or the like that has long batterystanding time, and the like can be obtained. Hereinafter, an embodimentof electronic devices incorporating a light-emitting device to which alight-emitting element of the present invention is applied is shown.

FIG. 5A is a computer manufactured by applying the present invention,which includes a main body 511, a casing 512, a display portion 513, akeyboard 514, and the like. The computer can be completed byincorporating the light-emitting device including the light-emittingelement of the present invention in the display portion.

FIG. 5B is a telephone manufactured by applying the present invention,in which a main body 522 includes a display portion 521, an audio outputportion 524, an audio input portion 525, operation switches 526 and 527,an antenna 523, and the like. The telephone can be completed byincorporating the light-emitting device including the light-emittingelement of the present invention in the display portion.

FIG. 5C is a television receiver set manufactured by applying thepresent invention, which includes a display portion 531, a casing 532, aspeaker 533, and the like. The television receiver set can be completedby incorporating the light-emitting device including the light-emittingelement of the present invention in the display portion.

As described above, the light-emitting devices of the present inventionare extremely suitable for the display portions of various kinds ofelectronic devices.

Although the computer and the like have been described in EmbodimentMode 5, the light-emitting device having the light-emitting element ofthe present invention may also be mounted in a navigation system, anillumination device, or the like.

Example 1

In Example 1, the electron-trapping property of an organometalliccomplex (a pyrazine-based organometallic complex) which can be used fora light-emitting element of the present invention was evaluated. Theorganometallic complex has a ligand having a pyrazine skeleton and acentral metal which is an element belonging to Group 9 or 10.

In the evaluation, reductive reaction characteristics of thepyrazine-based organometallic complex were measured by a cyclicvoltammetry (CV) measurement, and the LUMO level was calculated from theevaluation result. For comparison, the LUMO levels of a conventionalpyridine-based organometallic complex and substances serving as hostmaterials were calculated in the same way, and were compared to the LUMOlevel of the pyrazine-based organometallic complex. Note that anelectrochemical analyzer (ALS model 600A or 600C, manufactured by BASInc.) was used for the measurement.

As for a solution used in the CV measurement, dehydrateddimethylformamide (DMF, manufactured by Aldrich, 99.8%, catalog number:22705-6) was used as a solvent. Tetra-n-butylammonium perchlorate(n-Bu₄NClO₄, manufactured by Tokyo Chemical Industry Co., Ltd., catalognumber: T0836), which was a supporting electrolyte, was dissolved in thesolvent such that the concentration of the tetra-n-butylammoniumperchlorate was 100 mmol/L. Moreover, the object to be measured wasdissolved such that the concentration thereof was set to 1 mmol/L.Further, a platinum electrode (a PTE platinum electrode, manufactured byBAS Inc.) was used as a working electrode. A platinum electrode (a VC-3Pt counter electrode (5 cm), manufactured by BAS Inc.) was used as acounter electrode. An Ag/Ag+ electrode (an RE5 nonaqueous solventreference electrode, manufactured by BAS Inc.) was used as a referenceelectrode. It is to be noted that the measurement was conducted at roomtemperature (20 to 25° C.). In addition, the scan speed at the CVmeasurement was 0.1 V/sec.

(Calculation of Potential Energy with Respect to a Vacuum Level of aReference Electrode)

The potential energy (eV) with respect to a vacuum level of a referenceelectrode (Ag/Ag⁺ electrode) used in this example was calculated first.In other words, Fermi level of the Ag/Ag+ electrode was calculated. Itis known that the oxidation-reduction potential of ferrocene in methanolis +0.610 [V vs. SHE] with respect to the normal hydrogen electrode(Reference: Christian R. Goldsmith et al., J. Am. Chem. Soc., Vol. 124,No. 1, 83-96, 2002). On the other hand, when the oxidation-reductionpotential of ferrocene in methanol was calculated by using a referenceelectrode used in this example, it was +0.20 V [vs. Ag/Ag+]. Therefore,it was found that the potential energy of the reference electrode usedin this example was lower than that of the normal hydrogen electrode by0.41 [eV].

Note that it is known that the potential energy from the vacuum level ofthe normal hydrogen electrode is −4.44 eV (Reference: ONISHI. T et al.,High molecular EL materials—development of light-emitting high molecularcompounds-, 2004, pages 64-67, KYORITSU SHUPPAN). Accordingly, thepotential energy used in this example with respect to the vacuum levelof the reference electrode was as follows: −4.44-0.41=−4.85 [eV].

(Measurement Example: Structural formula (9))

In this measurement example, the calculation of the LUMO level by CVmeasurement is described taking Ir(tppr)₂(acac) represented by thestructural formula (9) as an example. FIG. 30 is a graph showing CVmeasurement results of reductive reaction characteristics. In themeasurement of the reductive reaction characteristics, the potential ofthe working electrode with respect to the reference electrode wasshifted from −0.34 to −2.40 V, and then, from −2.40 V to −0.34 V.

As illustrated in FIG. 30, the reduction peak potential E_(pc) was −1.88V. The oxidation peak potential E_(pa) was −1.82 V. Therefore, thehalf-wave potential (the intermediate potential between E_(pc) andE_(pa)) was calculated to be −1.85 V. This indicates thatIr(tppr)₂(acac) is reduced by an electric energy of −1.85 (V vs. Ag/Ag+)and this energy corresponds to the LUMO level. As described above, thepotential energy of the reference electrode used in Example 1 withrespect to the vacuum level was −4.85 [eV], and thus, it was found thatthe LUMO level of the pyrazine-based organometallic complex representedby the structural formula (9) was as follows: −4.85−(−1.85)=−3.00 [eV].

(Measurement Results)

In the same way, the LUMO level of the pyrazine-based organometalliccomplex disclosed in Embodiment Mode 3 was measured. For comparison, theLUMO levels of pyridine-based organometallic complexes such as[btpIr(acac)] (the following structural formula (I)) and Ir(ppy)₂(acac)(the following structural formula (II)) were measured. [btpIr(acac)] isan organometallic complex used in the Patent Document 1. In addition, asreference, the LUMO level of an electron-transporting compound BAlq (thefollowing structural formula (III)) which is widely used as a hostmaterial of a red phosphorescent compound was also evaluated.

The results are shown in Table 1. As seen from Table 1, as compared withthe pyridine-based organometallic complex ((I) to (III) in Table 1), allthe pyrazine-based organometallic complexes ((1), (3)-(9), (13)-(15),and (17) in Table 1) have deeper LUMO levels, which are deeper than −2.7eV. The LUMO levels of the pyrazine-based organometallic complexes aredeeper than that of BAlq. On the other hand, the pyridine-basedorganometallic complexes have a shallower LUMO level than that of BAlq.Therefore, from the results of this example, it is shown that thepyrazine-based organometallic complex used in the present invention hasa relatively high electron-trapping property.

TABLE 1 Structural Formula Substance E_(1/2) [V vs. LUMO level No.(abbreviation) Ag/Ag⁺] [eV] (1) Ir(dppr)₂(acac) −1.98 −2.87 (3)Ir(Fdppr)₂(acac) −1.92 −2.93 (4) Ir(Fdppr-Me)₂(acac) −2.00 −2.85 (5)Ir(Fdppr-Me)₂(pic) −1.82 −3.03 (6) Ir(Fdppr-Me)₂(bpz4) −1.86 −2.99 (7)Ir(Fdppr-iPr)₂(pic) −1.83 −3.02 (8) Ir(CF3dppr-Me)₂(pic) −1.63 −3.22 (9)Ir(tppr)₂(acac) −1.85 −3.00 (13)  Ir(dpqtH)₂(acac) −2.11 −2.74 (14) Ir(FdpqtH)₂(acac) −2.03 −2.82 (15)  Ir(FdpqtH)₂(pic) −1.90 −2.85 (17) Pt(FdpqtH)(acac) −1.81 −3.04 (I)  [btpIr(acac)] −2.39 −2.46 (II)Ir(ppy)₂(acac) −2.57 −2.28  (III) BAlq −2.31 −2.54

Example 2

Example 2 will specifically exemplify the light-emitting element of thepresent invention with reference to comparative examples. Molecularstructures of substances used in Example 2 are shown below. In addition,FIG. 3 illustrates a structure of the element.

<<Fabrication of a Light-Emitting Element 1 of the Present Invention, aLight-Emitting Element 2 of the Present Invention, a ComparativeLight-Emitting Element 3, and a Comparative Light-Emitting Element 4>>

First, a glass substrate on which a 110-nm-thick indium tin siliconoxide (ITSO) film was formed was prepared. The periphery of surface ofIMO was covered with a polyimide film so that the area, 2 mm×2 mm of thesurface was exposed. Note that ITSO was a first electrode 301 serving asan anode of the light-emitting element. As a pretreatment for formingthe light-emitting element, the surface of the substrate was washed witha porous resin brush, baked at 200° C. for one hour and was subjected toUV ozone treatment for 370 seconds.

Then, the substrate was fixed to a holder provided in a vacuumevaporation apparatus so that the surface provided with ITSO faceddownward.

After the pressure in the vacuum evaporation apparatus was reduced to10⁻⁴ Pa, NPB represented by the structural formula (I) andmolybdenum(VI) oxide were co-evaporated so as to satisfy NPB:molybdenum(VI) oxide=4:1 (mass ratio), whereby a hole-injecting layer 311 wasformed. The thickness thereof was 50 nm. Note that a co-evaporationmethod is an evaporation method in which a plurality of differentsubstances is concurrently vaporized from respective differentevaporation sources. Next, NPB was evaporated to be 10 nm thick, wherebya hole-transporting layer 312 was formed.

Further, over the hole-transporting layer 312, a light-emitting layer313 having a thickness of 30 nm was formed. Structures of thelight-emitting layer 313 of each of the light-emitting element 1, thelight-emitting element 2, the comparative light-emitting element 3 andthe comparative light-emitting element 4 are shown in Table 2. Thelight-emitting element 1 and the light-emitting element 2 arelight-emitting elements of the present invention, which employ NPB asthe first organic compound, BAlq represented by the structural formula(II) as the second organic compound, and Ir(tppr)₂(acac) represented bythe structural formula (9) in Embodiment Mode 3 as the pyrazine-basedorganic compound. As seen from Table 2, the ratio of NPB to BAlq isdifferent between the light-emitting element 1 and the light-emittingelement 2. On the other hand, the comparative light-emitting element 3employs only NPB as a host material without using BAlq. In addition, thecomparative light-emitting element 4 employs only BAlq as a hostmaterial without using NPB. The light-emitting layers 313 are all formedby a co-evaporation method.

TABLE 2 Ratio of the substances in the light- emitting layer (massratio) Light-emitting element 1 NPB:BAlq:Ir(tppr)₂(acac) = 0.25:1:0.06Light-emitting element 2 NPB:BAlq:Ir(tppr)₂(acac) = 0.10:1:0.06Comparative light-emitting NPB:Ir(tppr)₂(acac) = 1:0.06 element 3Comparative light-emitting BAlq:Ir(tppr)₂(acac) = 1:0.06 element 4

Then, BAlq was evaporated to be 10 nm thick over the light-emittinglayer 313, whereby an electron-transporting layer 314 was formed.Furthermore, over the electron-transporting layer 314, Alq₃ representedby the structural formula (iii) and lithium (Li) were co-evaporated soas to satisfy Alq₃:Li=1:0.01 (mass ratio), whereby an electron-injectinglayer 315 was formed. The thickness thereof was 50 nm. Finally, aluminumwas formed to be 200 nm thick as a second electrode 302 serving as acathode, whereby the light-emitting elements were obtained. Note that,in the above evaporation process, evaporation was all performed by aresistance heating method.

<<Operation Characteristics of the Light-Emitting Element 1, theLight-Emitting Element 2, the Comparative Light-Emitting Element 3 andthe Comparative Light-Emitting Element 4>>

After the light-emitting element 1, the light-emitting element 2, thecomparative light-emitting element 3 and the comparative light-emittingelement 4 obtained as described above were sealed in a glove box with anitrogen atmosphere so as not to be exposed to the air, operationcharacteristics of these light-emitting elements were measured. Notethat the measurement was performed at room temperature (an atmospherekept at 25° C.).

FIG. 6A shows current density-luminance characteristics of thelight-emitting elements, and FIG. 6B shows voltage-luminancecharacteristics thereof. FIG. 7 shows luminance-current efficiencycharacteristics of these light-emitting elements. FIG. 8 shows emissionspectra of these light-emitting elements. The emission spectra of thelight-emitting elements were almost the same, and emission was redemission derived from Ir(tppr)₂(acac). Note that as to only thecomparative light-emitting element 3, emission of BAlq was slightlyobserved around 480 nm.

As seen from FIG. 7, current efficiencies of the comparativelight-emitting element 3 and the comparative light-emitting element 4both drastically decrease in practical luminance region (100 cd/m² ormore). The comparative light-emitting element 3 is in the stateillustrated in FIG. 2A in Embodiment Mode 1. Since Ir(tppr)₂(acac)having a high electron-trapping property was added into NPB which was ahole-transporting compound, a light-emitting region was limited to thevicinity of the interface between the light-emitting layer 313 and theelectron-transporting layer 314. In the spectrum of the comparativelight-emitting element 3 of FIG. 8, emission of BAlq used for theelectron-transporting layer 314 is slightly observed. In other words, itis seen that holes reached the electron-transporting layer 314, whichcaused reduction of current efficiency. The comparative light-emittingelement 4 is in the state illustrated in FIG. 2B in Embodiment Mode 1.Since Ir(tppr)₂(acac) having a high electron-trapping property was addedinto BAlq which was an electron-transporting compound, it is consideredthat the carrier balance was bad and current efficiency was decreased.In addition, as apparent from FIG. 6B, driving voltage is high.

On the other hand, the light-emitting element 1 and the light-emittingelement 2 of the present invention exhibit extremely high emissionefficiency as apparent from FIG. 7. In particular, their externalquantum efficiencies are significant as apparent from Table 3, higherthan 20% at 1000 cd/m².

Next, the initial luminance was set at 1000 cd/m², and these elementswere driven at the constant current density. At that time, luminancedegradation curves as seen in FIG. 9 are obtained. FIG. 9 is a graph inwhich the horizontal axis represents time and the vertical axisrepresents relative luminance (%) when the initial luminance is 100. Asapparent from FIG. 9, the light-emitting elements of the presentinvention have greatly improved lifetime.

Table 3 shows the comparison in the characteristics at 1000 cd/m² andlifetime. Note that since it takes much time for the elements to reachthe luminance half-life period, the lifetimes of the elements arecompared, in terms of the period until which the luminance was reducedby 10%.

TABLE 3 External 10% Volt- Current quantum Power degradation ageEfficiency efficiency efficiency of luminance [V] [cd/A] [%] [lm/W] [hr]Light-emitting 5.0 24 21 15 640 element 1 Light-emitting 5.6 23 20 133,000^(※ ) element 2 Comparative 5.6 4.2 3.5 2.3 300 light-emittingelement 3 Comparative 6.6 12 10 5.6 240 light-emitting element 4*Extrapolation value

The current efficiency, the external quantum efficiency, and the powerefficiency were extremely low in the comparative light-emitting elementusing only NPB as a host material and in the comparative light-emittingelement 4 using only BAlq as a host material. On the contrary, thecurrent efficient, the external quantum efficiency, and the powerefficiency of the light-emitting element 1 and the light-emittingelement 2 using NPB and BAlq for the light-emitting layer were extremelyhigh, as apparent from Table 3. These results were not expected from thecharacteristics of NPB or BAlq which was used alone. The same can beapplied to the lifetime. In particular, the light-emitting element 2 canhave extremely long lifetime, and its luminance half-life period isestimated to be about 50,000 hours.

As described above, it can be found that the light-emitting elements ofthe present invention can achieve both high emission efficiency and longlifetime. Accordingly, by implementing the present invention,light-emitting elements having high emission efficiency and longlifetime can be provided.

Example 3

Example 3 will specifically describe a fabrication example of alight-emitting element (a light-emitting element 5) of the presentinvention. FIG. 3 illustrates a structure of the light-emitting element.

<<Fabrication of the Light-Emitting Element 5 of the Present Invention>>

The hole-injecting layer 311 and the hole-transporting layer 312 wereformed in the same way as those of the light-emitting element 1 inExample 2. The light-emitting layer 313 was formed over thehole-transporting layer 312. The light-emitting layer 313 includes NPBas the first organic compound, BAlq as the second organic compound, andIr(tppr)₂(acac) represented by the structural formula (9) in EmbodimentMode 3, as the pyrazine-based organometallic complex. The light-emittinglayer 313 was formed by co-evaporation such that the mass ratio isNPB:BAlq:Ir(tppr)₂(acac)=0.1:1:0.06. The thickness was 50 nm.

Next, a 10-nm-thick Alq₃ was evaporated to form theelectron-transporting layer 314. Over the electron-transporting layer314, Alq₃ and lithium (Li) were co-evaporated at the mass ratio ofAlq₃:Li=1:0.01 to form the electron-injecting layer 315. The thicknesswas 20 nm. Lastly, a 200-nm-thick aluminum was formed as the secondelectrode 302 serving as a cathode. In this manner, the light-emittingelement of the present invention was fabricated. All the aboveevaporation processes were conducted by resistance heating.

<<Operation Characteristics of the Light-Emitting Element 5>>

The thus obtained light-emitting element 5 was sealed in a glove boxwith a nitrogen atmosphere so as not to expose the light-emittingelements to the air, operation characteristics of the light-emittingelement were measured. Note that the measurement was performed at roomtemperature (an atmosphere kept at 25° C.).

FIG. 10A shows current density-luminance characteristics of thelight-emitting element 5, and FIG. 10B shows voltage-luminancecharacteristics thereof. FIG. 11 shows luminance-current efficiencycharacteristics and luminance-external quantum efficiencycharacteristics of the light-emitting element 5. FIG. 12 shows emissionspectrum of the light-emitting element 5. The emission spectrum of thelight-emitting element 5 was derived from Ir(tppr)₂(acac).

As seen from FIG. 12, the peak of the emission spectrum of thelight-emitting element 5 is around 620 nm, and the light-emittingelement 5 exhibited red emission whose CIE chromaticity coordinates were(x, y)=(0.65, 0.35).

Also, as seen from FIG. 11, the current efficiency of the light-emittingelement 5 of the present invention reached a maximum, 30 cd/A at 200cd/m², which was extremely high efficiency. The external quantumefficiency in this case was 23%. Further, at the 1000 cd/m² which wasregarded as a practical luminance region, the current efficiency was 27cd/A (the external quantum efficiency was 20%) and extremely highefficiency.

The light-emitting element 5 uses Alq₃ having a lower triplet excitationenergy than Ir(tppr)₂(acac) (emission wavelength: 620 nm or less)serving as a light-emitting substance, as the electron-transportinglayer 314 in contact with the light-emitting layer 313. Despite this,high efficiency that the external quantum efficiency is higher than 20%as described above can be achieved. This suggests that thelight-emitting region in the light-emitting element of the presentinvention does not locate only at the interface between thelight-emitting layer 313 and the electron-transporting layer 314. Thisis also one feature of the present invention.

Next, the initial luminance was set at 1000 cd/m², and the element wasdriven at the constant current density. At that time, a luminancedegradation curve as seen in FIG. 13 is obtained. FIG. 13 is a graph inwhich the horizontal axis represents time and the vertical axisrepresents relative luminance (%) when the initial luminance is 100. Asapparent from FIG. 13, the light-emitting element 5 of the presentinvention has extremely long lifetime, since 10% degradation time ofluminance was estimated at as long as 4000 hours from an extrapolationvalue of the curve in FIG. 13. In addition, its luminance half-lifeperiod is estimated to be about 100,000 hours.

Example 4

Example 4 will specifically exemplify the light-emitting element of thepresent invention with reference to comparative examples. In addition,FIG. 3 illustrates a structure of the element.

<<Fabrication of a Light-Emitting Element 6, a ComparativeLight-Emitting Element 7 and a Comparative Light-Emitting Element 8>>

A light-emitting element 6 of the present invention was fabricated inthe same way as the light-emitting element 2 of Example 2, except thatIr(tppr)₂(acac) of the light-emitting layer 313 was changed toIr(dppr)₂(acac) (the structural formula (I) in Embodiment Mode 3), andthat the thickness of the electron-injecting layer 315 was 40 nm. Inaddition, the comparative light-emitting element 7 was fabricated in thesame way as the comparative light-emitting element 3 of Example 2,except that Ir(tppr)₂(acac) of the light-emitting layer 313 was changedto Ir(dppr)₂(acac), and that the thickness of the electron-injectinglayer 315 was 40 nm. In addition, the comparative light-emitting element8 was fabricated in the same way as the comparative light-emittingelement 4 of Example 2, except that Ir(tppr)₂(acac) of thelight-emitting layer 313 was changed to Ir(dppr)₂(acac), and that thethickness of the electron-injecting layer 315 was 40 nm. In summary, thelight-emitting element 6, the comparative light-emitting element 7 andthe comparative light-emitting element 8 have different structures ofthe light-emitting layer 313 from one another as shown in Table 4, butthe other layers than the light-emitting layer 313 were fabricated inthe same way.

TABLE 4 Ratio of substances in the light- emitting layer (mass ratio)Light-emitting element 6 NPB:BAlq:Ir(dppr)₂(acac) = 0.10:1:0.06Comparative light-emitting NPB:Ir(dppr)₂(acac) = 1:0.06 element 7Comparative light-emitting BAlq:Ir(dppr)₂(acac) = 1:0.06 element 8<<Operation Characteristics of the Light-Emitting Element 6, theComparative Light-Emitting Element 7 and the Comparative Light-EmittingElement 8>>

The thus obtained light-emitting element 6, comparative light-emittingelement 7 and comparative light-emitting element 8 were sealed in aglove box with a nitrogen atmosphere so as not to expose thelight-emitting elements to the air, operation characteristics of thelight-emitting elements were measured. Note that the measurement wasperformed at room temperature (an atmosphere kept at 25° C.).

FIG. 14A shows current density-luminance characteristics of thelight-emitting elements, and FIG. 14B shows voltage-luminancecharacteristics thereof. FIG. 15 shows luminance-current efficiencycharacteristics of the light-emitting elements. FIG. 16 shows emissionspectra of the light-emitting elements. The emission spectra of thelight-emitting elements were almost the same and emission was orange,which was derived from Ir(dppr)₂(acac) (Note that only the comparativelight-emitting element 7 slightly emitted light with a shortwavelength.).

As apparent from FIG. 15, the current efficiency of the comparativelight-emitting element 8 is decreased in the practical luminance region(100 cd/m² or more). The comparative light-emitting element 8 is in thestate illustrated in FIG. 2B in Embodiment Mode 1. Since Ir(dppr)₂(acac)having a high electron-trapping property is added into BAlq which is anelectron-transporting compound, it is considered that the carrierbalance is bad and current efficiency is decreased. In addition, asapparent from FIG. 14B, driving voltage is high.

The comparative light-emitting element 7 has a mode similar to the modeof FIG. 2A; however, its initial characteristics are almost the same asthose of the light-emitting element 6 of the present invention. Thisseems to be because emission of BAlq used for the electron-transportinglayer 314 was not observed, unlike the comparative light-emittingelement 3 of Example 2. As seen from Example 1, Ir(dppr)₂(acac) used inExample 4 has a weaker electron-trapping property than Ir(tppr)₂(acac)used in Example 2. Thus, it is inferred that in the comparativelight-emitting element 7, more or less electrons reached the inside ofthe light-emitting layer 313, and emission of BAlq used for theelectron-transporting layer 314 was suppressed.

However, surprisingly, the remarkable difference of the lifetime betweenthe light-emitting element 6 of the present invention and thecomparative light-emitting element 7 was seen. The initial luminance wasset at 1000 cd/m², and these elements were driven at the constantcurrent density. Luminance degradation curves in this case are shown inFIG. 17. FIG. 17 is a graph in which the horizontal axis represents timeand the vertical axis represents relative luminance (%) when the initialluminance is 100. As apparent from FIG. 17, only the light-emittingelement 6 of the present invention has greatly improved lifetime.

The comparison of characteristics at 1000 cd/m² and lifetime is shown inTable 5.

TABLE 5 External Luminance Volt- Current quantum Power half-life ageEfficiency efficiency efficiency period [V] [cd/A] [%] [lm/W] [hr]Light-emitting 6.2 28 15 14 4,100*  element 6 Comparative 5.6 28 14 16 84 light-emitting element 7 Comparative 6.8 16 8.0 7.4 190light-emitting element 8 *Extrapolation value

As seen in Table 5, the current efficiency, the external quantumefficiency, and the power efficiency were extremely low in thecomparative light-emitting element 8 using only BAlq as a host material,while the current efficiency, the external quantum efficiency, and thepower efficiency were extremely high in the light-emitting element 6using two kinds, NPB and BAlq as a host material and in the comparativelight-emitting element 7 using only NPB as a host material. As for thelifetime, the luminance half-life period of the comparativelight-emitting element 7 and the comparative light-emitting element 8are both around 100 hours, while the luminance half-life period of thelight-emitting element 6 of the present invention is estimated to beabout 4000 hours from an extrapolation value.

In particular, although the light-emitting element 6 and the comparativelight-emitting element 7 have almost the same initial characteristics,the lifetime of the light-emitting elements are remarkably different,which is an amazing result. The cause is not surely ascertained;however, it is thought that in the comparative light-emitting element 7,the excitation state of BAlq used for the electron-transporting layer314 may influence on the lifetime due to the light-emitting region insome way.

As described above, it can be found that the light-emitting element ofthe present invention can achieve both high emission efficiency and longlifetime. Accordingly, by implementing the present invention, alight-emitting element having high emission efficiency and long lifetimecan be provided.

Example 5

Example 5 will specifically exemplify the light-emitting element of thepresent invention with reference to a comparative example. In addition,FIG. 3 illustrates a structure of the element.

<<Fabrication of a Light-Emitting Element 9 and a ComparativeLight-Emitting Element 10>>

A light-emitting element 9 of the present invention was fabricated inthe same way as the light-emitting element 2 of Example 2, except thatBAlq of the light-emitting layer 313 was changed to CO11 represented bythe structural formula (Iv). Note that the ratio of NPB, CO11 and Ir(tppr)₂(acac) was NPB: CO11: Ir(tppr)₂(acac)=0.5:1:0.06 (mass ratio). Inaddition, a comparative light-emitting element 10 was fabricated in thesame way as the comparative light-emitting element 3 of Example 2,except that BAlq of the light-emitting layer 313 was changed to CO11.CO11 is a heteroaromatic compound having a 1,3,4-oxadiazole skeleton.

<<Operation Characteristics of the Light-Emitting Element 9 and theComparative Light-Emitting Element 10>>

The thus obtained light-emitting element 9 and the comparativelight-emitting element 10 were sealed in a glove box with a nitrogenatmosphere so as not to expose the light-emitting elements to the air,operation characteristics of the light-emitting element were measured.Note that the measurement was performed at room temperature (anatmosphere kept at 25° C.).

FIG. 18A shows current density-luminance characteristics of thelight-emitting elements, and FIG. 18B shows voltage-luminancecharacteristics thereof. FIG. 19 shows luminance-current efficiencycharacteristics of the light-emitting elements. FIG. 20 shows emissionspectra of the light-emitting elements. The emission spectra of thelight-emitting elements were almost the same and emission was red, whichwas derived from Ir(tppr)₂(acac).

As seen from FIG. 19, the current efficiency of the comparativelight-emitting element 10 is decreased in the practical luminance region(100 cd/m² or more). The comparative light-emitting element 10 is in thestate illustrated in FIG. 2B in Embodiment Mode 1. Since Ir(tppr)₂(acac)having a high electron-trapping property is added into CO11 which is anelectron-transporting compound, it is considered that the carrierbalance is bad and current efficiency is decreased. In addition, asapparent from FIG. 18B, driving voltage is high. On the other hand, thelight-emitting element 9 of the present invention exhibited highemission efficiency as apparent from FIG. 19.

Next, the initial luminance was set at 1000 cd/m², and these elementswere driven at the constant current density. Thus, luminance degradationcurves as seen in FIG. 21 are obtained. FIG. 21 is a graph in which thehorizontal axis represents time and the vertical axis representsrelative luminance (%) when the initial luminance is 100. As apparentfrom FIG. 21, the light-emitting element of the present invention hasgreatly improved lifetime. The comparison of characteristics at 1000cd/m² and lifetime is shown in Table 6.

TABLE 6 External Luminance Volt- Current quantum Power half-life ageEfficiency efficiency efficiency period [V] [cd/A] [%] [lm/W] [hr]Light-emitting 4.4 22 17 16 2,900* element 9 Comparative 7.0 12 10 5.4  230* light-emitting element 10 *Extrapolation value

As described above, it can be found that the light-emitting element ofthe present invention can achieve both high emission efficiency and longlifetime. Accordingly, by implementing the present invention, alight-emitting element having high emission efficiency and long lifetimecan be provided.

Example 6

Example 6 will specifically exemplify the light-emitting element of thepresent invention with reference to a comparative example. In addition,FIG. 3 illustrates a structure of the element.

<<Fabrication of a Light-Emitting Element 11 of the Present Inventionand a Comparative Light-Emitting Element 12>.

A light-emitting element 11 of the present invention was fabricated inthe same way as the light-emitting element 2 of Example 2, except thatBAlq of the light-emitting layer 313 was changed to CzQn represented bythe structural formula (V). Note that the ratio of NPB, CzQn and Ir(tppr)₂(acac) was NPB:CzQn: Ir(tppr)₂(acac)=0.25:1:0.06 (mass ratio). Inaddition, a comparative light-emitting element 12 was fabricated in thesame way as the comparative light-emitting element 3 of Example 2,except that BAlq of the light-emitting layer 313 was changed to CzQn.CzQn is a heteroaromatic compound having a quinoxaline skeleton.

<<Operation Characteristics of the Light-Emitting Element 11 and theComparative light-Emitting Element 12>>

The thus obtained light-emitting element 11 and the comparativelight-emitting element 12 were sealed in a glove box with a nitrogenatmosphere so as not to expose the light-emitting elements to the air,operation characteristics of the light-emitting elements were measured.Note that the measurement was performed at room temperature (anatmosphere kept at 25° C.).

FIG. 22A shows current density-luminance characteristics of thelight-emitting elements, and FIG. 22B shows voltage-luminancecharacteristics thereof. FIG. 23 shows luminance-current efficiencycharacteristics of the light-emitting elements. FIG. 24 shows emissionspectra of the light-emitting elements. The emission spectra of thelight-emitting elements were almost the same and emission was red, whichwas derived from Ir(tppr)₂(acac).

As apparent from FIG. 23, the current efficiency of the comparativelight-emitting element 12 is decreased in the practical luminance region(100 cd/m² or more). The comparative light-emitting element 12 is in thestate illustrated in FIG. 2B in Embodiment Mode 1. Since Ir(tppr)₂(acac)having a high electron-trapping property was added into CzQn which wasan electron-transporting compound, it is considered that the carrierbalance was bad and current efficiency was decreased. In addition, asapparent from FIG. 22B, driving voltage is high. On the other hand, thelight-emitting element 11 of the present invention exhibited highemission efficiency as apparent from FIG. 23.

Next, the initial luminance was set at 1000 cd/m², and these elementswere driven at the constant current density. At that time, luminancedegradation curves as seen in FIG. 25 was obtained. FIG. 25 is a graphin which the horizontal axis represents time and the vertical axisrepresents relative luminance (%) when the initial luminance is 100. Asapparent from FIG. 25, the light-emitting element of the presentinvention has greatly improved lifetime. The comparison ofcharacteristics at 1000 cd/m² and lifetime is shown in Table 7.

TABLE 7 External Luminance Volt- Current quantum Power half-life ageEfficiency efficiency efficiency period [V] [cd/A] [%] [lm/W] [hr]Light-emitting 6.0 19 15 10 2,600* element 11 Comparative 8.6 4.4 3.51.6   310* light-emitting element 12 *Extrapolation value

As described above, it can be found that the light-emitting element ofthe present invention can achieve both high emission efficiency and longlifetime. Accordingly, by implementing the present invention, alight-emitting element having high emission efficiency and long lifetimecan be provided.

Example 7

Example 7 will specifically exemplify the light-emitting element of thepresent invention with reference to a comparative example. In addition,FIG. 3 illustrates a structure of the element.

<<Fabrication of a Light-Emitting Element 13 of the Present Inventionand a Comparative Light-Emitting Element 14>>

A light-emitting element 13 of the present invention was fabricated inthe same way as the light-emitting element 2 of Example 2, except thatBAlq of the light-emitting layer 313 was changed to DCzPQ represented bythe structural formula (Vi). Note that the ratio of NPB, DCzPQ and Ir(tppr)₂(acac) was NPB:DCzPQ:Ir(tppr)₂(acac)=0.5:1:0.06 (mass ratio). Inaddition, a comparative light-emitting element 14 was fabricated in thesame way as the comparative light-emitting element 3 of Example 2,except that BAlq of the light-emitting layer 313 was changed to DCzPQ.DCzPQ is a heteroaromatic compound having a quinoxaline skeleton.

<<Operation Characteristics of the Light-Emitting Element 13 and theComparative Light-Emitting Element 14>>

The thus obtained light-emitting element 13 and the comparativelight-emitting element 14 were sealed in a glove box with a nitrogenatmosphere so as not to expose the light-emitting elements to the air,operation characteristics of the light-emitting elements were measured.Note that the measurement was performed at room temperature (anatmosphere kept at 25° C.).

FIG. 26A shows current density-luminance characteristics of thelight-emitting elements, and FIG. 26B shows voltage-luminancecharacteristics thereof. FIG. 27 shows luminance-current efficiencycharacteristics of the light-emitting elements. FIG. 28 shows emissionspectra of the light-emitting elements. The emission spectra of thelight-emitting elements were almost the same and emission was red, whichwas derived from Ir(tppr)₂(acac).

As seen from FIG. 27, the current efficiency of the comparativelight-emitting element 14 is decreased in the practical luminance region(100 cd/m² or more). The comparative light-emitting element 14 is in thestate illustrated in FIG. 2B in Embodiment Mode 1. Since Ir(tppr)₂(acac)having a high electron-trapping property was added into DCzPQ which wasan electron-transporting compound, it is considered that the carrierbalance was bad and current efficiency was decreased. In addition, asapparent from FIG. 26B, driving voltage is high. On the other hand, thelight-emitting element 13 of the present invention exhibited highemission efficiency as apparent from FIG. 27.

Next, the initial luminance was 1000 cd/m², and these elements weredriven at the constant current density. At that time, luminancedegradation curves as seen in FIG. 29 was obtained. FIG. 29 is a graphin which the horizontal axis represents time and the vertical axisrepresents relative luminance (%) when the initial luminance is 100. Asapparent from FIG. 29, the light-emitting element of the presentinvention has greatly improved lifetime. The comparison ofcharacteristics at 1000 cd/m² and lifetime is shown in Table 8.

TABLE 8 External Volt- Current quantum Power Luminance age Efficiencyefficiency efficiency half-life [V] [cd/A] [%] [lm/W] period [hr]Light-emitting 5.6 18 14 10 2,200* element 13 Comparative 8.8 3.0 2.51.1   180* light-emitting element 14 *Extrapolation value

As described above, it can be found that the light-emitting element ofthe present invention can achieve both high emission efficiency and longlifetime. Accordingly, by implementing the present invention, alight-emitting element having high emission efficiency and long lifetimecan be provided.

Example 8

Example 8 will specifically exemplify the light-emitting element of thepresent invention with reference to a comparative example. In addition,FIG. 3 illustrates a structure of the element.

<<Fabrication of a Light-Emitting Element 15 of the Present Inventionand a Comparative Light-Emitting Element 16>>

The hole-injecting layer 311 and the hole-transporting layer 312 wereformed in the same way as those of the light-emitting element 1 inExample 2. The light-emitting layer 313 was formed over thehole-transporting layer 312. In the light-emitting element 15 of thepresent invention, the light-emitting layer 313 includes NPB as thefirst organic compound, BAlq as the second organic compound and(acetylacetonato)bis[5-(3-fluorophenyl)-2,3-diphenylpyrazinato]iridium(III)(abbreviation: [Ir(dppr-3FP)₂(acac)]), represented by the structuralformula (18), as the pyrazine-based organometallic complex. Thelight-emitting layer 313 was formed by co-evaporation such that the massratio is NPB:BAlq:Ir(dppr-3FP)₂(acac)=0.05:1:0.06. The thickness was 50nm. On the other hand, in the comparative light-emitting element 16, thelight-emitting layer 313 was formed by co-evaporation such that the massratio, BAlq:Ir(dppr-3FP)₂(acac)=1:0.06, without using NPB. The thicknessof the light-emitting layer 313 was 50 nm. Note that Ir(dppr-3FP)₂(acac)is a kind of organometallic complexes represented by the general formula(G6) in Embodiment Mode 3.

Next, a 30-nm-thick Alq₃ was evaporated to form theelectron-transporting layer 314. Over the electron-transporting layer314, a 1-nm-thick lithium fluoride (LiF) was evaporated to form theelectron-injecting layer 315. Lastly, a 200-nm-thick aluminum was formedas the second electrode 302 serving as a cathode. In this manner, thelight-emitting element 15 of the present invention and the comparativelight-emitting element 16 were fabricated. All the above evaporationprocesses were conducted by resistance heating.

<<Operation Characteristics of the Light-Emitting Element 15 and theComparative Light-Emitting Element 16>>

The thus obtained light-emitting element 15 and the comparativelight-emitting element 16 were sealed in a glove box with a nitrogenatmosphere so as not to expose the light-emitting elements to the air,operation characteristics of the light-emitting elements were measured.Note that the measurement was performed at room temperature (anatmosphere kept at 25° C.).

FIG. 33A shows current density-luminance characteristics of thelight-emitting elements, and FIG. 33B shows voltage-luminancecharacteristics thereof. FIG. 34 shows luminance-current efficiencycharacteristics of the light-emitting elements. FIG. 35 shows emissionspectra of the light-emitting elements. From the emission spectra, it isfound that red emission from the both light-emitting elements wasobserved, which was derived from Ir(dppr-3Fp)₂(acac). Note that CIEchromaticity coordinates of the light-emitting element 15 was (x,y)=(0.67, 0.33), and the coordinates correspond to the red coordinatesof red color according to NTSC. Thus, the light-emitting elementsexhibited favorable red emission.

Next, the initial luminance was set at 1000 cd/m², and these elementswere driven at the constant current density. At that time, luminancedegradation curves as seen in FIG. 36 were obtained. FIG. 36 is a graphin which the horizontal axis represents time and the vertical axisrepresents relative luminance (%) when the initial luminance is 100. Asapparent from FIG. 36, the light-emitting element of the presentinvention have greatly improved lifetime. The comparison ofcharacteristics at 1000 cd/m² and lifetime is shown in Table 9. Notethat it appears to take 10000 hours or more for the light-emittingelement 15 to reach the luminance half-life period as apparent from FIG.36, and thus the lifetime of the light-emitting element is compared interms of the period in which the luminance decreased to 86%.

TABLE 9 The period in External Power which the Volt- Current quantumeffi- luminance age Efficiency efficiency ciency decreased to [V] [cd/A][%] [lm/W] 86% [hr] Light-emitting 8.8 18 16 6.3 2,200* element 15Comparative 9.2 6.9 5.8 2.4   180* light-emitting element 16*Extrapolation value

As described above, it can be found that the light-emitting element ofthe present invention can achieve both high emission efficiency and longlifetime. Accordingly, by implementing the present invention, alight-emitting element having high emission efficiency and long lifetimecan be provided.

In this example, a novel substance,(acetylacetonato)bis[5-(3-fluorophenyl)-2,3-diphenylpyrazinato]iridium(III)(abbreviation: Ir(dppr-3FP)₂(acac) was used. Thus, a synthesis examplethereof will be described specifically.

Step 1: Synthesis of 5-(3-fluorophenyl)-2,3-diphenylpyrazine(abbreviation Hdppr-3FP)

In a nitrogen atmosphere, 7.5 mL of a hexane solution of n-butyllithium(1.58 mol/L) was dropped into a mixed solution of 1.49 g of3-bromofluorobenzene and 11 mL of tetrahydrofuran at −78° C. and stirredfor 30 minutes at −78° C. The obtained solution was dropped into a mixedsolution, which was cooled by ice, of 2.45 g of 2,3-diphenylpyrazine and20 mL of tetrahydrofuran, and stirred for one hour at room temperature.Water was added into this mixture and an organic layer was extracted asethyl acetate using an extraction solvent. The obtained organic layerwas washed with water, and dried with anhydrous magnesium. The solutionafter drying was filtrated. The solvent of the solution was distilledoff and the residue obtained by distillation was refined with a silicagel column chromatography using dichloromethane as a developing solvent.In this way, an objective pyrazine derivative, Hdppr-3FP (orange powder,yield: 8%) was obtained. The synthesis scheme of Step 1 is shown by(a-1).

Step 2: Synthesis ofdi-μ-chloro-bis[bis{5-(3-fluorophenyl)-2,3-diphenylpyrazinato}iridium(III)](abbreviation: [Ir(dppr-3FP)₂Cl]₂)

Subsequently to Step 1, 4.5 mL of 2-ethoxyethanol, 1.5 mL of water, 0.40g of the pyrazine derivative, Hdppr-3FP obtained in Step 1, and 0.18 gof iridium chloride hydrate (IrCl₃.H₂O) (manufactured by Sigma-AldrichCorp.) were put in an egg plant flask attached with a reflux tube, andthe inside of the flask was substituted by argon. After that, it wassubjected to microwave (2.45 GHz, 200 W) for five hours to be reacted.Orange powder precipitated from the reaction solution was filtrated andwashed with ethanol to form a binuclear complex, [Ir(dppr-3FP)₂Cl]₂(yield: 12%). A microwave synthesizer (Discovery, manufactured by CEMcorporation) was used for the irradiation of microwave. The synthesisscheme of Step 2 is shown by (b-1).

Step 3 Synthesis of(acetylacetonato)bis[5-(3-fluorophenyl)-2,3-diphenylpyrazinato]iridium(III)(abbreviation: [Ir(dppr-3FP)₂(acac)]

Subsequently to Step 2, 5 mL of 2-ethoxyethanol, 0.13 g of the binuclearcomplex, [Ir(dppr-3FP)₂Cl]₂ obtained in Step 2, 0.02 mL ofacetylacetone, and 0.078 g of sodium carbonate were put in an egg plantflask attached with a reflux tube, and the inside of the flask wassubstituted by argon. After that, it was subjected to a microwave (2.45GHz 200 W) for 15 minutes to be reacted. The reaction solution wasfiltrated, and the solvent of the obtained filtrate was distilled off.The residue obtained by distillation was recrystallized by methanol. Inthis way, [Ir(dppr-3FP)₂(acac) was obtained (red powder, yield: 100%).The synthesis scheme of Step 3 is shown by (c-1).

This application is based on Japanese Patent Application serial no.2006-325057 filed in Japan Patent Office on Nov. 30, 2006, the entirecontents of which are hereby incorporated by reference.

The invention claimed is:
 1. A light-emitting device comprising: a holetransporting layer and an electron transporting layer between a firstelectrode and a second electrode; a light-emitting layer between thehole transporting layer and the electron transporting layer, wherein thelight-emitting layer includes a first organic compound having ahole-transporting property, a second organic compound having an electrontransporting property, and an organometallic complex, wherein the firstorganic compound, the second organic compound, and the organometalliccomplex are mixed with each other, wherein a central metal of theorganometallic complex is an element belonging to one of Group 9 andGroup 10, wherein a ligand of the organometallic complex has a pyrazineskeleton, wherein a LUMO level of the organometallic complex is deeperthan a LUMO level of the first organic compound and a LUMO level of thesecond organic compound by 0.2 eV or more, and wherein a HOMO level ofthe organometallic complex is located between a HOMO level of the firstorganic compound and a HOMO level of the second organic compound.
 2. Thelight-emitting device according to claim 1, wherein the ligand is a2-arylpyrazine derivative.
 3. The light-emitting device according toclaim 1, wherein the ligand is a 2-phenylpyrazine derivative.
 4. Thelight-emitting device according to claim 1, wherein the ligand is a2,5-diphenylpyrazine derivative.
 5. The light-emitting device accordingto claim 1, wherein the central metal is one of iridium and platinum,the first organic compound is one of an aromatic amine compound and acarbazole derivative, and the second organic compound is one of aheteroaromatic compound and a metal complex.
 6. The light-emittingdevice according to claim 1, wherein an amount of the organometalliccomplex in the light-emitting layer is greater than or equal to 1percent by mass and less than or equal to 10 percent by mass.
 7. Thelight-emitting device according to claim 1, wherein the light-emittingdevice is incorporated in one selected from the group consisting of anillumination device, a computer, a telephone and a television set. 8.The light-emitting device according to claim 1, wherein the holetransporting layer includes an anthracene derivative.
 9. Alight-emitting device comprising: a hole transporting layer and anelectron transporting layer between a first electrode and a secondelectrode; a light-emitting layer between the hole transporting layerand the electron transporting layer, wherein the light-emitting layerincludes a first organic compound having a hole-transporting property, asecond organic compound having an electron transporting property, and anorganometallic complex, wherein the first organic compound, the secondorganic compound, and the organometallic complex are mixed with eachother, wherein the organometallic complex is represented by a generalformula (G1),

wherein A_(r) represents an arylene group, R¹ represents one of an alkylgroup and an aryl group, R² represents one of hydrogen, an alkyl groupand an aryl group, R³ represents one of hydrogen and an alkyl group, Mis a central metal, and the M represents an element belonging to one ofGroup 9 and Group 10, wherein a LUMO level of the organometallic complexis deeper than a LUMO level of the first organic compound and a LUMOlevel of the second organic compound by 0.2 eV or more, and wherein aHOMO level of the organometallic complex is located between a HOMO levelof the first organic compound and a HOMO level of the second organiccompound.
 10. The light-emitting device according to claim 9, whereinthe R² and the R³ are bound to each other to form an alicycle.
 11. Thelight-emitting device according to claim 9, wherein the Ar isrepresented by a general formula (G2), and

wherein R⁴ to R⁷ each represent one of hydrogen, an alkyl group, ahalogen group, a haloalkyl group, an alkoxy group, and an alkoxycarbonylgroup.
 12. The light-emitting device according to claim 9, wherein theAr is represented by a general formula (G2),

wherein the R² is represented by a general formula (G3), and

wherein R⁴ to R¹² each represent one of hydrogen, an alkyl group, ahalogen group, a haloalkyl group, an alkoxy group, and an alkoxycarbonylgroup.
 13. The light-emitting device according to claim 9, wherein the Mis one of iridium and platinum, the first organic compound is one of anaromatic amine compound and a carbazole derivative, and the secondorganic compound is one of a heteroaromatic compound and a metalcomplex.
 14. The light-emitting device according to claim 9, wherein anamount of the organometallic complex in the light-emitting layer isgreater than or equal to 1 percent by mass and less than or equal to 10percent by mass.
 15. The light-emitting device according to claim 9,wherein the light-emitting device is incorporated in one selected fromthe group consisting of an illumination device, a computer, a telephoneand a television set.
 16. The light-emitting device according to claim9, wherein the hole transporting layer includes an anthracenederivative.
 17. A light-emitting device comprising: a hole transportinglayer and an electron transporting layer between a first electrode and asecond electrode; a light-emitting layer between the hole transportinglayer and the electron transporting layer, wherein the light-emittinglayer includes a first organic compound having a hole-transportingproperty, a second organic compound having an electron transportingproperty, and an organometallic complex, wherein the first organiccompound, the second organic compound, and the organometallic complexare mixed with each other, wherein the organometallic complex isrepresented by a general formula (G4),

wherein A_(r) represents an arylene group, R¹ represents one of an alkylgroup and an aryl group, R² represents one of hydrogen, an alkyl groupand an aryl group, R³ represents one of hydrogen and an alkyl group, Mis a central metal, the M represents an element belonging to one ofGroup 9 and Group 10, and L represents a monoanionic ligand, whereinwhen the M is an element belonging to Group 9, n is 2 and when the M isan element belonging to Group 10, n is 1, wherein a LUMO level of theorganometallic complex is deeper than a LUMO level of the first organiccompound and a LUMO level of the second organic compound by 0.2 eV ormore, and wherein a HOMO level of the organometallic complex is locatedbetween a HOMO level of the first organic compound and a HOMO level ofthe second organic compound.
 18. The light-emitting device according toclaim 17, wherein the R² and the R³ are bound to each other to form analicycle.
 19. The light-emitting device according to claim 17, whereinthe Ar is represented by a general formula (G5), and

wherein R⁴ to R⁷ each represent one of hydrogen, an alkyl group, ahalogen group, a haloalkyl group, an alkoxy group, and an alkoxycarbonylgroup.
 20. The light-emitting device according to claim 17, wherein theAr is represented by a general formula (G5),

wherein the R² is represented by a general formula (G6), and

wherein R⁴ to R¹² each represent one of hydrogen, an alkyl group, ahalogen group, a haloalkyl group, an alkoxy group, and an alkoxycarbonylgroup.
 21. The light-emitting device according to claim 17, wherein theM is one of iridium and platinum, the first organic compound is one ofan aromatic amine compound and a carbazole derivative, and the secondorganic compound is one of a heteroaromatic compound and a metalcomplex.
 22. The light-emitting device according to claim 17, wherein anamount of the organometallic complex in the light-emitting layer isgreater than or equal to 1 percent by mass and less than or equal to 10percent by mass.
 23. The light-emitting device according to claim 17,wherein the light-emitting device is incorporated in one selected fromthe group consisting of an illumination device, a computer, a telephoneand a television set.
 24. The light-emitting device according to claim17, wherein the hole transporting layer includes an anthracenederivative.